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532-65-0 Usage

Description

ar-Turmerone is a sesquiterpenoid compound characterized by the presence of a 2-methylhept-2-en-4-one structure, with a 4-methylphenyl group substitution at position 6. It has been isolated from the plant Peltophorum dasyrachis and holds potential applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
ar-Turmerone is used as a bioactive compound for its potential therapeutic effects. ar-Turmerone has demonstrated anti-inflammatory, antioxidant, and neuroprotective properties, making it a promising candidate for the development of new drugs targeting various health conditions.
Used in Cosmetic Industry:
In the cosmetic industry, ar-Turmerone is used as an ingredient for its anti-inflammatory and antioxidant properties. It can be incorporated into skincare products to help reduce inflammation, protect the skin from oxidative stress, and promote overall skin health.
Used in Flavor and Fragrance Industry:
Due to its unique aroma and flavor profile, ar-Turmerone is used as a component in the flavor and fragrance industry. It can be utilized to create natural and complex scents for perfumes, as well as to enhance the taste and aroma of various food products.
Used in Agricultural Industry:
ar-Turmerone's bioactive properties also make it a potential candidate for use in the agricultural industry. It could be employed as a natural pesticide or fungicide, helping to protect crops from pests and diseases while minimizing the environmental impact of synthetic chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 2909, 1973 DOI: 10.1021/jo00956a039Synthetic Communications, 11, p. 579, 1981 DOI: 10.1080/00397918108063627Tetrahedron Letters, 20, p. 1519, 1979 DOI: 10.1016/S0040-4039(01)86195-5

Check Digit Verification of cas no

The CAS Registry Mumber 532-65-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 2 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 532-65:
(5*5)+(4*3)+(3*2)+(2*6)+(1*5)=60
60 % 10 = 0
So 532-65-0 is a valid CAS Registry Number.
InChI:InChI=1/C15H22O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5-7,9,13-14H,8,10H2,1-4H3

532-65-0 Well-known Company Product Price

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  • Sigma-Aldrich

  • (42258)  (S)-ar-Turmerone  analytical standard

  • 532-65-0

  • 42258-10MG

  • 5,564.52CNY

  • Detail

532-65-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (+)-(S)-ar-turmerone

1.2 Other means of identification

Product number -
Other names Tumerone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:532-65-0 SDS

532-65-0Synthetic route

(6S)-2-methyl-6-p-tolylhept-2-en-4-ol

(6S)-2-methyl-6-p-tolylhept-2-en-4-ol

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
With manganese(IV) oxide In tetrachloromethane at 60℃; for 0.5h;94%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 0℃; Swern oxidation;53%
With pyridinium chlorochromate In dichloromethane for 1h; Ambient temperature; 3A molecular sieves;52%
(S)-(+)-iso-ar-turmerone
77732-37-7

(S)-(+)-iso-ar-turmerone

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
With piperidine In diethyl ether93%
dimethyl (S)-(2-oxo-4-(p-tolyl)pentyl)phosphonate

dimethyl (S)-(2-oxo-4-(p-tolyl)pentyl)phosphonate

acetone
67-64-1

acetone

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
With potassium carbonate In ethanol at 50℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction;89%
N-methoxy-N-methyl-3-p-tolyl-butyramide

N-methoxy-N-methyl-3-p-tolyl-butyramide

2-methyl-1-propenylbromide
3017-69-4

2-methyl-1-propenylbromide

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
Stage #1: 2-methyl-1-propenylbromide With iodine; magnesium In tetrahydrofuran Inert atmosphere; Schlenk technique; Glovebox; Reflux;
Stage #2: N-methoxy-N-methyl-3-p-tolyl-butyramide In tetrahydrofuran at -15 - 20℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox;
88%
(6R)-2-methyl-5-(phenylsulfonyl)-6-p-tolylhept-2-en-4-one

(6R)-2-methyl-5-(phenylsulfonyl)-6-p-tolylhept-2-en-4-one

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
With diethylamine; naphthalen-1-yl-lithium In tetrahydrofuran at -78℃; Inert atmosphere;85%
2-methyl-1-propenylbromide
3017-69-4

2-methyl-1-propenylbromide

Lithium; 3-p-tolyl-butyrate

Lithium; 3-p-tolyl-butyrate

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
In diethyl ether for 24h;69.9%
(S)-1-(1-methyl-1H-imidazol-2-yl)-3-(p-tolyl)butan-1-one

(S)-1-(1-methyl-1H-imidazol-2-yl)-3-(p-tolyl)butan-1-one

2-methylpropen-1-ylmagnesium bromide
38614-36-7

2-methylpropen-1-ylmagnesium bromide

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
Stage #1: (S)-1-(1-methyl-1H-imidazol-2-yl)-3-(p-tolyl)butan-1-one; 2-methylpropen-1-ylmagnesium bromide In tetrahydrofuran at 0 - 20℃; for 2.16667h; Inert atmosphere;
Stage #2: With methyl iodide In ethyl acetate at 60℃; for 16h; Inert atmosphere;
Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 80℃; Inert atmosphere;
61%
Methyl 3,3-dimethylacrylate
924-50-5

Methyl 3,3-dimethylacrylate

(S)-2,2'-(2-(p-tolyl)propane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

(S)-2,2'-(2-(p-tolyl)propane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
Stage #1: (S)-2,2'-(2-(p-tolyl)propane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere;
Stage #2: Methyl 3,3-dimethylacrylate In tetrahydrofuran at 50℃; for 0.5h; Inert atmosphere;
Stage #3: With water In tetrahydrofuran for 0.25h; Inert atmosphere; Acidic conditions;
40%
(S)-4-(4-methylphenyl)-2-pentanone
69657-27-8

(S)-4-(4-methylphenyl)-2-pentanone

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
With sodium ethanolate; acetone
(S)-4-(4-methylphenyl)-2-pentanone
69657-27-8

(S)-4-(4-methylphenyl)-2-pentanone

sodium ethanolate
141-52-6

sodium ethanolate

acetone
67-64-1

acetone

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
[(2)H6]acetone
666-52-4

[(2)H6]acetone

bisacurone B
127214-85-1

bisacurone B

A

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

B

C18H22(2)H6O3

C18H22(2)H6O3

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 1h; Ambient temperature;
(+)-(7S,9R)-ar-turmerol
120710-98-7

(+)-(7S,9R)-ar-turmerol

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

Conditions
ConditionsYield
With manganese(IV) oxide In tetrachloromethane at 60℃; for 0.5h;
bisacurone A
127214-84-0

bisacurone A

A

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

B

intermedin B
127214-87-3

intermedin B

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane for 1h; Ambient temperature;
bisacurone B
127214-85-1

bisacurone B

A

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

B

C18H22(2)H6O3

C18H22(2)H6O3

Conditions
ConditionsYield
With (CD3)CO; toluene-4-sulfonic acid for 1h; Ambient temperature;
bisacurone
120681-81-4

bisacurone

A

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

B

intermedin B
127214-87-3

intermedin B

C

(S)-2-Methyl-6-((3aS,5R,7aR)-2,2,7a-trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-hept-2-en-4-one
127304-87-4

(S)-2-Methyl-6-((3aS,5R,7aR)-2,2,7a-trimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl)-hept-2-en-4-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone for 1h; Ambient temperature;
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

formyl-ar-turmerone

formyl-ar-turmerone

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at 0 - 20℃; for 2h;83%
(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

(S)-2-methylpropane-2-sulfinamide
343338-28-3

(S)-2-methylpropane-2-sulfinamide

C19H29NOS
1425093-38-4

C19H29NOS

Conditions
ConditionsYield
With titanium(IV) tetraethanolate at 70℃; for 12h;64%
With titanium(IV) tetraethanolate at 70℃; for 12h;64%
(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

(R)-2-methylpropane-2-sulfinamide
196929-78-9

(R)-2-methylpropane-2-sulfinamide

C19H29NOS
1425371-12-5

C19H29NOS

Conditions
ConditionsYield
With titanium(IV) tetraethanolate at 70℃; for 12h;63%
With titanium(IV) tetraethanolate at 70℃; for 12h;63%
(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

isobutylamine
78-81-9

isobutylamine

(6S)-N-isobutyl-2-methyl-6-(p-tolyl)hept-2-en-4-amine
1263273-08-0

(6S)-N-isobutyl-2-methyl-6-(p-tolyl)hept-2-en-4-amine

Conditions
ConditionsYield
Stage #1: (+)-(S)-ar-turmerone; isobutylamine With titanium tetrachloride In dichloromethane at -78℃; for 2h;
Stage #2: With sodium tetrahydroborate In dichloromethane at 0℃; for 0.5h;
51%
(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

A

(S)-6-(2-hydroxy-4-methylphenyl)-2-methylhept-2-en-4-one
131651-38-2

(S)-6-(2-hydroxy-4-methylphenyl)-2-methylhept-2-en-4-one

B

(S)-turmeronol A
131651-37-1

(S)-turmeronol A

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; Phthaloyl dichloride at 50℃; for 48h;A 7%
B 15%
(+)-(S)-ar-turmerone
532-65-0

(+)-(S)-ar-turmerone

(S)-ar-turmerone semicarbazone
109650-88-6

(S)-ar-turmerone semicarbazone

Conditions
ConditionsYield

532-65-0Relevant articles and documents

Access to Chiral HWE Reagents by Rhodium-Catalyzed Asymmetric Arylation of γ,δ-Unsaturated β-Ketophosphonates

Yin, Long,Zhang, Dewei,Xing, Junhao,Wang, Yuhan,Wu, Changhui,Lu, Tao,Chen, Yadong,Hayashi, Tamio,Dou, Xiaowei

, p. 5869 - 5875 (2018)

Asymmetric arylation of ?,?-unsaturated β-ketophosphonates with arylboronic acids is reported. By using the (R)-diene? ligated rhodium(I) chloride complex as a catalyst under none basic conditions, the corresponding β-ketophosphonates bearing a ?-chiral center were obtained in high yields (up to 99%) with good to excellent enantioselectivities (up to >99% ee). The enantioenriched products can be readily converted to diverse chiral β′-aryl enones by the Horner-Wadsworth-Emmons reaction.

Cobalt-Catalyzed Enantioselective Synthesis of Chiral gem-Bis(boryl)alkanes

Teo, Wei Jie,Ge, Shaozhong

supporting information, p. 12935 - 12939 (2018/09/20)

We report an asymmetric synthesis of enantioenriched gem-bis(boryl)alkanes in an enantioselective diborylation of 1,1-disubstituted alkenes catalyzed by Co(acac)2/(R)-DM-segphos. A range of activated and unactivated alkenes underwent this asymmetric diborylation in the presence of cyclooctene as a hydrogen acceptor, affording the corresponding gem-bis(boryl)alkanes with high enantioselectivity. The synthetic utility of these chiral organoboronate compounds was demonstrated through several stereospecific derivatizations and the synthesis of sesquiterpene and sesquiterpenoid natural products.

Highly efficient Rh-catalyzed asymmetric hydrogenation of α,β-unsaturated nitriles

Yan, Qiaozhi,Kong, Duanyang,Li, Meina,Hou, Guohua,Zi, Guofu

, p. 10177 - 10181 (2015/09/01)

A highly efficient enantioselective hydrogenation of α,β-unsaturated nitriles catalyzed by Rh-(R,R)-f-spiroPhos complex has been developed. With Rh-(R,R)-f-spiroPhos catalyst and under mild conditions, a wide range of α,β-unsaturated nitriles including the (E)- and (Z)-isomers of 3-alkyl-3-aryl, 3,3-diaryl, and 3,3-dialkyl α,β-unsaturated nitriles were hydrogenated to the corresponding chiral nitriles with excellent enantioselectivities (up to 99.9% ee) and high turnover numbers (TON up to 10,000).

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