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Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-

Cas:4674-50-4

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Hubei CuiRan Biotechnology Co., Ltd

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medicine)

Nootkatone

Cas:4674-50-4

Min.Order:10 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

High Content Natural Extract (+)-Nootkatone HACCP manufacturer

Cas:4674-50-4

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe

nootkatone

Cas:4674-50-4

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Nootkatone

Cas:4674-50-4

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin

NOOTKATONE CAS:4674-50-4

Cas:4674-50-4

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

inquiry

Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Pharmaceutical Grade CAS 4674-50-4 with fast shipping

Cas:4674-50-4

Min.Order:10 Gram

FOB Price: $146.0 / 176.0

Type:Trading Company

inquiry

Wuhan Han Sheng New Material Technology Co.,Ltd

Our Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We

NOOTKATONE/FEMA No. 3166 4674-50-4

Cas:4674-50-4

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

inquiry

Shanghai Upbio Tech Co.,Ltd

1.In No Less 10 years exporting experience. you can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specializ

2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)-

Cas:4674-50-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Qingdao Beluga Import and Export Co., LTD

NOOTKATONE CAS:4674-50-4 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates,

NOOTKATONE CAS:4674-50-4

Cas:4674-50-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Nootkatone

Cas:4674-50-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Lonwin Chemical Group Limited

NOOTKATONE CAS: 4674-50-4 Specification Item Standard Source Pure natural plant extract Sterilization method No irradiation Production Environmen

Factory supply NOOTKATONE

Cas:4674-50-4

Min.Order:1 Kilogram

Negotiable

Type:Other

inquiry

Leader Biochemical Group

PRODUCT DETAILS

China Largest Manufacturer factory Supply NOOTKATONE CAS 4674-50-4

Cas:4674-50-4

Min.Order:500 Kilogram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Factory Supply Nootkatone

Cas:4674-50-4

Min.Order:0 Metric Ton

Negotiable

Type:Other

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

High purity 4674-50-4 low price Nootkatone Direct Manufacturer Round pomelone is a sesquiterpene ketone isolated from grapefruit peel oil and Alaskan phellodendron oil. It is a colorless or light yellow oily liquid with a melting point of 35~36 ℃

High purity 4674-50-4 low price Nootkatone Direct Manufacturer

Cas:4674-50-4

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

High Quality 2(3H)-Naphthalenone,4,4a,5,6,7,8-hexahydro-4,4a-dimethyl-6-(1-methylethenyl)-, (4R,4aS,6R)

Cas:4674-50-4

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

SHANGHAI SYSTEAM BIOCHEM CO., LTD

We are one of a few suppliers that can offer custom synthesis service of this product We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to prov

NOOTKATONE

Cas:4674-50-4

Min.Order:100 Gram

FOB Price: $100.0 / 2000.0

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

1)quick response within 12 hours; 2)quality guarantee: all products are strictly tested by our qc, confirmed by qa and approved by third party lab in china, usa, canada, germany, uk, italy, france etc. 3) oem/odm available; 4) rea

NOOTKATONECAS NO.: 4674-50-4

Cas:4674-50-4

Min.Order:1 Kilogram

FOB Price: $4.0

Type:Lab/Research institutions

inquiry

EAST CHEMSOURCES LIMITED

factory?direct?saleAppearance:White Powder Storage:Store In Dry, Cool And Ventilated Place Package:25kg/drum, also according to the clients requirement Application:It is widely used as a thickener, emulsifier and stabilizer Transportation:By Sea Or B

NOOTKATONE

Cas:4674-50-4

Min.Order:1 Kilogram

FOB Price: $18.0 / 20.0

Type:Trading Company

inquiry

Shandong Mopai Biotechnology Co., LTD

Shandong Mopai Biotechnology Co., LTD is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemicals. W

NOOTKATONE

Cas:4674-50-4

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

KAISA GROUP INC

1.Applied in food field.it can improve the immune system and prolong life. 2.Appliedin cosmetic field.it can improve the skin care. 3.Applied in pharmaceutical field.it can treat various dieases. 4.Our product quality assurance will make our customer

NOOTKATONE

Cas:4674-50-4

Min.Order:1 Metric Ton

FOB Price: $1.5

Type:Trading Company

inquiry

Henan Tianfu Chemical Co., Ltd.

Our advantage:Our company was built in 2009 with an ISO certificate.In the past 5 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientif

TIANFU-CHEM NOOTKATONE

Cas:4674-50-4

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hefei Zhaobo Technology Co., Ltd.

Nootkatone is mainly used to prepare various citrus flavors. Appearance:colorless crystal Storage:cool dry place Package:1.Weight <1kg ---- Fluorinated bottle 2. 25kg ---- Drum we accept packaging customization. Application:Nootkatone is mainly us

Food grade Flavoring Agents food additive powder Cas 4674-50-4 nootkatone

Cas:4674-50-4

Min.Order:1 Kilogram

FOB Price: $1.0 / 50.0

Type:Trading Company

inquiry

Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&amp;D and production as well as custom synthesis for chemical products and chemical business project. We are supp

NOOTKATONE

Cas:4674-50-4

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Trading Company

inquiry

Wuxi TAA Chemical Industry Co.,LTD.

1.A strong technical force and advanced processing equipments. The quality of the products has been strictly inspected and all kinds of index have reached or exceeded domestic and international standards.2. Now we have established long-term stable re

NOOTKATONE CAS 4674-50-4

Cas:4674-50-4

Min.Order:0

Negotiable

Type:Other

inquiry

Sinoway Industrial Co., Ltd.

Why is SINOWAY:1) Specialized in pharmaceutical and healthcare industrial since 19872) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days.4) We have warehouse in USA with quickly shipment . Application:Herbal extr

Hangzhou Dingyan Chem Co., Ltd

high purity, manufacturer Application:Intermediate

Nootkatone, (+)-

Cas:4674-50-4

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Shanghai Acmec Biochemical Technology Co., Ltd.

Acmec is a leading manufacturer and supplier of biochemical reagents and life science products. We have over 40,000 items in stock (real-time inventory) and offer discounted prices to registered members of the online store ( www.acmec.com.cn ) Appea

Acmec (+)-Nootkatone 20mg

Cas:4674-50-4

Min.Order:1 bottle

Negotiable

Type:Lab/Research institutions

inquiry

Henan Allgreen Chemical Co.,Ltd

high quality Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea

Nootkatone

Cas:4674-50-4

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Chengdu Lemeitian Pharmaceutical Technology Co,. Ltd

ADVANTAGE:1. More than 3,000 Chinese medicine reference substances / standard products available from stock, issued on the same day, multiple cities can be delivered the next day2. The products are provided with COA, HPLC, NMR, quality assurance, pac

Nootkatone

Cas:4674-50-4

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Synthetic route

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone
72453-44-2

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
With sodium acetate In water; acetic acid at 100℃; for 2h;93%
With sodium acetate; acetic acid at 100℃; for 2h; Inert atmosphere;93%
With sodium acetate; acetic acid at 100℃; for 2h;93%
With aluminum oxide In hexane at 60℃; for 24h; Yield given;
semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Stage #1: valencene With manganese(IV) oxide In dichloromethane at -25℃; for 0.5h;
Stage #2: With tert.-butylhydroperoxide In dichloromethane; water at -10℃; for 9h; Reflux;
Stage #3: semicarbazide hydrochloride Further stages;
83%
Conditions
ConditionsYield
With Czapek-pepton medium; Pallavicinia subcilita at 30℃; for 168h; pH=7.0;82%
With pyridine; tert.-butylhydroperoxide; N-hydroxy-3,4,5,6-tetrachlorophthalimide; lithium perchlorate In acetone Reagent/catalyst; Solvent; Electrochemical reaction; chemoselective reaction;77%
With tert.-butylhydroperoxide; sodium chlorite In water; acetonitrile at 50℃; for 18h; Product distribution / selectivity;72%

A

phthalimide
136918-14-4

phthalimide

B

(+)-nootkatone
4674-50-4

(+)-nootkatone

C

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol
840474-83-1

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol

Conditions
ConditionsYield
With oxygen; N-hydroxyphthalimide; cobalt nitrate; cobalt(II) acetate; cobalt(III) acetylacetonate In acetonitrile at 40℃; under 9750.98 Torr; for 3h; Product distribution / selectivity;A n/a
B 67.9%
C 5.6%
With oxygen; N-hydroxyphthalimide; cobalt(II) acetate; cobalt(III) acetylacetonate In acetonitrile at 40℃; under 9750.98 Torr; for 4h; Product distribution / selectivity;A n/a
B 53.7%
C 1.4%
(4R,4aS,6R)-2-hydroperoxy-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalene
329309-57-1

(4R,4aS,6R)-2-hydroperoxy-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalene

A

(+)-nootkatone
4674-50-4

(+)-nootkatone

B

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol
840474-83-1

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol

Conditions
ConditionsYield
With lyophilisate of Pleurotus sapidus In aq. buffer at 20℃; for 48h; pH=7.4; Enzymatic reaction;A 16%
B 7%
Conditions
ConditionsYield
With culture medium of Mucor species; Czapek-pepton medium at 30℃; for 168h;A 0.7%
B 0.6%
(4R,6R,10S)-4,10-dimethyl-6-(1‘-hydroxyisopropyl)-1-en-3,4,5,6,7,8-hexahydronaphthalen-2-one
20489-50-3

(4R,6R,10S)-4,10-dimethyl-6-(1‘-hydroxyisopropyl)-1-en-3,4,5,6,7,8-hexahydronaphthalen-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
With pyridine; trichlorophosphate
(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone
72453-44-2

(4R,4aS,6R)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-chloro-1-methylethyl)-2(3H)-naphthalenone

A

(4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one
15764-04-2

(4R,4aS)-(+)-4,4a-dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one

B

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
With aluminum oxide In hexane at 60℃; for 24h;

A

(2R,4aR,8R,8aS)-2-Isopropenyl-8,8a-dimethyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-ol
50763-63-8

(2R,4aR,8R,8aS)-2-Isopropenyl-8,8a-dimethyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a-ol

B

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol
50763-66-1

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

C

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol
50763-67-2

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

D

(+)-nootkatone
4674-50-4

(+)-nootkatone

E

(4R,4aS,6R)-6-Isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ol
32420-34-1, 32420-35-2, 50763-64-9, 50763-65-0, 53643-08-6

(4R,4aS,6R)-6-Isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydro-naphthalen-1-ol

Conditions
ConditionsYield
Mechanism; Product distribution; multistep reaction: photooxygenation + reduction; reaction with triplet and singlet oxygen;
2-Methyl-4-isopropenyl-6-n-butylthiomethylen-cyclohexanon
67779-29-7

2-Methyl-4-isopropenyl-6-n-butylthiomethylen-cyclohexanon

trans-3-penten-2-one
3102-33-8

trans-3-penten-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
(i) KOtBu, tBuOH, (ii) aq. KOH; Multistep reaction;
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

A

(+)-nootkatone
4674-50-4

(+)-nootkatone

B

2β-t-butylperoxy-4α,5α,7β-eremophila-1(10),11-diene

2β-t-butylperoxy-4α,5α,7β-eremophila-1(10),11-diene

C

9β-t-butylperoxy-2-oxo-4α,5α,7β-eremophila-1(10),11-diene

9β-t-butylperoxy-2-oxo-4α,5α,7β-eremophila-1(10),11-diene

Conditions
ConditionsYield
With copper(l) iodide In acetonitrile at 50℃; for 18h; Substitution; oxydation;A 260 mg
B 31 mg
C n/a

A

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol
50763-67-2

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

B

(+)-nootkatone
4674-50-4

(+)-nootkatone

C

(-)-2-(2R)-(1,2,3,4,6,7,8,8a-octahydro-8α,8aβ-dimethyl-2α-naphthalenyl)-2-propen-1-ol

(-)-2-(2R)-(1,2,3,4,6,7,8,8a-octahydro-8α,8aβ-dimethyl-2α-naphthalenyl)-2-propen-1-ol

Conditions
ConditionsYield
With chicory; enzymes from roots of Cichorium intybus L; NADPH In ethanol for 1h; pH=7.5; Product distribution; Further Variations:; Reagents;

A

(+)-(4R,5S,7R,11S)-11,12-epoksynootkatone

(+)-(4R,5S,7R,11S)-11,12-epoksynootkatone

B

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol
50763-66-1

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

C

(+)-nootkatone
4674-50-4

(+)-nootkatone

D

(1aR,4R,4aS,6R,8aS)-4,4a-dimethyl-6-(prop-1-en-2-yl)octahydro-1aH-naphtho[1,8a-b]oxirene

(1aR,4R,4aS,6R,8aS)-4,4a-dimethyl-6-(prop-1-en-2-yl)octahydro-1aH-naphtho[1,8a-b]oxirene

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; cytochrome P450BM-3 Product distribution; Enzyme kinetics; Further Variations:; Reagents;

A

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol
50763-67-2

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

B

(+)-nootkatone
4674-50-4

(+)-nootkatone

C

9α-hydroxy-2-oxo-4α,5α,7β-eremophila-1(10),11-diene
226546-99-2

9α-hydroxy-2-oxo-4α,5α,7β-eremophila-1(10),11-diene

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; cytochrome P450cam In ethanol Product distribution; Enzyme kinetics; Further Variations:; Reagents;

A

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol
50763-66-1

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

B

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol
50763-67-2

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

C

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
With Botryosphaeria dothidea (Ume BD8398II); Czapek-pepton medium at 30℃; for 168h; pH=7.0;A 31 % Chromat.
B 18 % Chromat.
C 43 % Chromat.
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol
50763-66-1

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2β-ol

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
With Chlorella pyrenoidosa for 24h;
4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol
50763-67-2

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
With Chlorella fusca for 24h;
Multi-step reaction with 2 steps
1: 42 percent / p-nitrobenzoic acid; triphenylphosphine; diethyl azodicarboxylate
2: Chlorella pyrenoidosa / 24 h
View Scheme
(1R,5S)-(+)-nopinone
38651-65-9

(1R,5S)-(+)-nopinone

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 88 percent / triethylamine / dimethylformamide / 24 h / 95 °C
2: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C
3: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
4: 81 percent / TiCl4 / CH2Cl2
5: 71 percent / NaNH2 / benzene
6: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
7: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
8: Al2O3 / hexane / 24 h / 60 °C
View Scheme
Multi-step reaction with 8 steps
1: 88 percent / triethylamine / dimethylformamide / 24 h / 95 °C
2: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C
3: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
4: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C
5: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
6: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
7: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
8: Al2O3 / hexane / 24 h / 60 °C
View Scheme
Multi-step reaction with 7 steps
1: 55 percent / N-methylaniline, EtMgBr / benzene; diethyl ether / 1 h / 0 °C
2: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
3: 81 percent / TiCl4 / CH2Cl2
4: 71 percent / NaNH2 / benzene
5: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
6: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
7: Al2O3 / hexane / 24 h / 60 °C
View Scheme
(1R,3S,5R)-3-<(1R)-1-Methyl-3-oxobutyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one
72453-41-9

(1R,3S,5R)-3-<(1R)-1-Methyl-3-oxobutyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
2: Al2O3 / hexane / 24 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; hydrogenchloride / 21 h / 20 °C / Inert atmosphere
2: acetic acid; sodium acetate / 2 h / 100 °C
View Scheme
(1R,3R,5R)-6,6-Dimethyl-3-(1-hydroxyethyl)bicyclo<3.1.1>heptan-2-one
72453-38-4, 72541-05-0, 73068-69-6

(1R,3R,5R)-6,6-Dimethyl-3-(1-hydroxyethyl)bicyclo<3.1.1>heptan-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
2: 81 percent / TiCl4 / CH2Cl2
3: 71 percent / NaNH2 / benzene
4: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
6: Al2O3 / hexane / 24 h / 60 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
2: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C
3: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
4: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
6: Al2O3 / hexane / 24 h / 60 °C
View Scheme
(1R,5R)-6,6-Dimethyl-2-<(trimethylsilyl)oxy>bicyclo<3.1.1>hept-2-ene
72453-33-9

(1R,5R)-6,6-Dimethyl-2-<(trimethylsilyl)oxy>bicyclo<3.1.1>hept-2-ene

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C
2: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
3: 81 percent / TiCl4 / CH2Cl2
4: 71 percent / NaNH2 / benzene
5: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
6: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
7: Al2O3 / hexane / 24 h / 60 °C
View Scheme
Multi-step reaction with 7 steps
1: 96 percent / TiCl4 / CH2Cl2 / 1.5 h / -78 °C
2: 90 percent / p-toluenesulfonic acid / benzene / 2 h / Heating
3: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C
4: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
5: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
6: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
7: Al2O3 / hexane / 24 h / 60 °C
View Scheme
(1R,3S,5S)-6,6-Dimethyl-3-<1-methyl-3-butenyl>bicyclo<3.1.1>heptan-2-one
72453-39-5, 72541-06-1, 73068-72-1, 73068-73-2, 75657-63-5

(1R,3S,5S)-6,6-Dimethyl-3-<1-methyl-3-butenyl>bicyclo<3.1.1>heptan-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
2: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
3: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
4: Al2O3 / hexane / 24 h / 60 °C
View Scheme
(1R,3S,5S)-6,6-Dimethyl-3-<1-methyl-3-methyl-3-butenyl>bicyclo<3.1.1.>heptan-2-one
72453-42-0, 72541-07-2, 73068-70-9, 73068-71-0, 75657-65-7

(1R,3S,5S)-6,6-Dimethyl-3-<1-methyl-3-methyl-3-butenyl>bicyclo<3.1.1.>heptan-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 71 percent / NaNH2 / benzene
2: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
3: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
4: Al2O3 / hexane / 24 h / 60 °C
View Scheme
(1R,3S,5R)-3-<1-Methyl-3-butenyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one
72453-40-8, 72521-66-5, 75657-64-6

(1R,3S,5R)-3-<1-Methyl-3-butenyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
2: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
3: Al2O3 / hexane / 24 h / 60 °C
View Scheme
(1R,3S,5R)-3-<1-Methyl-3-methyl-3-butenyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one
72453-43-1, 72541-08-3, 75657-66-8

(1R,3S,5R)-3-<1-Methyl-3-methyl-3-butenyl>-3,6,6-trimethylbicyclo<3.1.1>heptan-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
2: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
3: Al2O3 / hexane / 24 h / 60 °C
View Scheme
(1R,5R)-6,6-Dimethyl-3-(Z)-ethylidenebicyclo<3.1.1>heptan-2-one
73068-31-2

(1R,5R)-6,6-Dimethyl-3-(Z)-ethylidenebicyclo<3.1.1>heptan-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: p-toluenesulfonic acid monohydrate / ethanol / 3 h / Ambient temperature
2: 81 percent / TiCl4 / CH2Cl2
3: 71 percent / NaNH2 / benzene
4: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
6: Al2O3 / hexane / 24 h / 60 °C
View Scheme
Multi-step reaction with 6 steps
1: p-toluenesulfonic acid monohydrate / ethanol / 3 h / Ambient temperature
2: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C
3: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
4: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
5: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
6: Al2O3 / hexane / 24 h / 60 °C
View Scheme
(1R,5R)-6,6-Dimethyl-3-(E)-ethylidenebicyclo<3.1.1>heptan-2-one
72453-37-3

(1R,5R)-6,6-Dimethyl-3-(E)-ethylidenebicyclo<3.1.1>heptan-2-one

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 81 percent / TiCl4 / CH2Cl2
2: 71 percent / NaNH2 / benzene
3: 1.) O3; 2.) Zn/CH3COOH / 1.) -78 deg C, 30 min; 2.) room temperature overnight.
4: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
5: Al2O3 / hexane / 24 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1: 89 percent / TiCl4 / CH2Cl2 / 2 h / -78 °C
2: 72 percent / NaNH2 / benzene / 1.) reflux, 5 h; 2.) 45 deg C, 17.5 h.
3: 1.) mercuric acetate; 2.) LiCl, PdCl2, CuCl2. / 1.) room temperature, CH3OH, 15 min; 2.) 55 deg C, CH3OH, 1 hour.
4: 73 percent / HCl / acetic acid / 21 h / Ambient temperature
5: Al2O3 / hexane / 24 h / 60 °C
View Scheme
Multi-step reaction with 6 steps
1.1: magnesium / tetrahydrofuran / 0.5 h / Reflux
1.2: -78 °C
2.1: potassium hydride; 18-crown-6 ether / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere
3.1: sodium amide / benzene / 5 h / Inert atmosphere; Reflux
3.2: 17.5 h / 45 °C
4.1: acetic acid; zinc / dichloromethane / 5 h / -78 - 30 °C / Inert atmosphere
5.1: acetic acid; hydrogenchloride / 21 h / 20 °C / Inert atmosphere
6.1: acetic acid; sodium acetate / 2 h / 100 °C
View Scheme
2-Methyl-4-isopropenyl-6-hydroxymethylen-cyclohexanon
67779-36-6

2-Methyl-4-isopropenyl-6-hydroxymethylen-cyclohexanon

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TsOH
2: (i) KOtBu, tBuOH, (ii) aq. KOH
View Scheme
(+)-(2R,4R)-2-methyl-4-isopropenylcyclohexanone
118710-90-0

(+)-(2R,4R)-2-methyl-4-isopropenylcyclohexanone

(+)-nootkatone
4674-50-4

(+)-nootkatone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaOMe, MeOH
2: TsOH
3: (i) KOtBu, tBuOH, (ii) aq. KOH
View Scheme
(+)-nootkatone
4674-50-4

(+)-nootkatone

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol
840474-83-1

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 4.33333h; Time;98.3%
(+)-nootkatone
4674-50-4

(+)-nootkatone

6-isopropyl-4,4a-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one
5195-69-7

6-isopropyl-4,4a-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalen-2(1H)-one

Conditions
ConditionsYield
With Wilkinson's catalyst; hydrogen In benzene at 20℃; for 8h;96%
With Wilkinson's catalyst; hydrogen In benzene for 14h; Ambient temperature;81%
With Wilkinson's catalyst; hydrogen In benzene for 14h; Ambient temperature;81%
With tris(triphenylphosphine)rhodium(l) chloride; hydrogen In benzene for 8h;
With Wilkinson's catalyst; hydrogen under 5250.53 Torr; for 2h;
(+)-nootkatone
4674-50-4

(+)-nootkatone

6-isopropenyl-4,4a-dimethyl-3,4,5,6,7,8-hexahydro-1aH-naphtho[1,8a-b]oxiren-2-one
439112-90-0

6-isopropenyl-4,4a-dimethyl-3,4,5,6,7,8-hexahydro-1aH-naphtho[1,8a-b]oxiren-2-one

Conditions
ConditionsYield
With dihydrogen peroxide; sodium hydroxide96%
(+)-nootkatone
4674-50-4

(+)-nootkatone

lithium tetramethyl alanate
14281-94-8, 32661-49-7, 32661-50-0

lithium tetramethyl alanate

(4R,4aS,6R)-6-Isopropenyl-2,4,4a-trimethyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-2-ol

(4R,4aS,6R)-6-Isopropenyl-2,4,4a-trimethyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-2-ol

Conditions
ConditionsYield
copper(I) bromide In tetrahydrofuran; diethyl ether 0.5 h at 0 deg C, 6 h at room temp.;94%
(+)-nootkatone
4674-50-4

(+)-nootkatone

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

(3R,4aS,5R)-7-ethynyl-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5-hexahydronaphthalene
1449115-27-8

(3R,4aS,5R)-7-ethynyl-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5-hexahydronaphthalene

Conditions
ConditionsYield
Stage #1: (+)-nootkatone With N,N-phenylbistrifluoromethane-sulfonimide; lithium hexamethyldisilazane at -78℃; Inert atmosphere;
Stage #2: acetylenemagnesium bromide With tetrakis(triphenylphosphine) palladium(0) at 20℃; Inert atmosphere;
94%
(+)-nootkatone
4674-50-4

(+)-nootkatone

fluoro-(+)-nootkatone

fluoro-(+)-nootkatone

Conditions
ConditionsYield
With HO4S(1-)*K(1+)*13FH In 1,2-dichloro-ethane at 0 - 20℃; for 2h; regioselective reaction;94%
(+)-nootkatone
4674-50-4

(+)-nootkatone

(+)-cis-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2-(3H)-naphthalenone
51557-49-4

(+)-cis-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-2-(3H)-naphthalenone

Conditions
ConditionsYield
Stage #1: (+)-nootkatone With methanol; ozone
Stage #2: With ferrous(II) sulfate heptahydrate; thiophenol at -78 - 20℃; for 0.5h;
94%
(+)-nootkatone
4674-50-4

(+)-nootkatone

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol
50763-67-2

4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol

Conditions
ConditionsYield
With sodium tetrahydroborate; cerium(III) chloride heptahydrate In methanol at 23℃; for 0.166667h; Inert atmosphere;91%
With sodium tetrahydroborate; cerium(III) chloride87%
With sodium tetrahydroborate; cerium(III) chloride In ethanol at 20℃; for 1h;82.7%
(+)-nootkatone
4674-50-4

(+)-nootkatone

C15H22Cl2

C15H22Cl2

Conditions
ConditionsYield
With C26H24Cl2P2(2+)*CH2Cl2*2C2H4Cl2*Cl5Sb(2-); water In nitromethane at 23℃; for 16h; Inert atmosphere;91%
trimethylaluminum
75-24-1

trimethylaluminum

(+)-nootkatone
4674-50-4

(+)-nootkatone

A

(3R,4aS,5R)-3-Isopropenyl-4a,5,7-trimethyl-1,2,3,4,4a,5-hexahydro-naphthalene

(3R,4aS,5R)-3-Isopropenyl-4a,5,7-trimethyl-1,2,3,4,4a,5-hexahydro-naphthalene

B

(4R,4aS,6R)-6-Isopropenyl-4,4a,8a-trimethyl-octahydro-naphthalen-2-one

(4R,4aS,6R)-6-Isopropenyl-4,4a,8a-trimethyl-octahydro-naphthalen-2-one

Conditions
ConditionsYield
copper(I) bromide In tetrahydrofuran for 22h; Ambient temperature;A 90%
B 2%
bis(acetylacetonate)nickel(II) In tetrahydrofuran for 4.5h; Ambient temperature;A 17%
B 77%
(+)-nootkatone
4674-50-4

(+)-nootkatone

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

Conditions
ConditionsYield
Stage #1: (+)-nootkatone With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride at 20℃; Inert atmosphere;
Stage #2: acetylenemagnesium bromide With tetrakis(triphenylphosphine) palladium(0) at 20℃; Inert atmosphere;
88%

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