gamma-Nonanolactone supplier

Name
gamma-Nonanolactone
EINECS 203-219-1
CAS No. 104-61-0
Article Data46
CAS DataBase
Density 0.956 g/cm³
Solubility 9.22g/L(25 oC)
Melting Point
Formula C₉H₁₆O₂
Boiling Point 266.6 °C at 760 mmHg
Molecular Weight 156.225
Flash Point 98.8 °C
Transport Information
Appearance
Safety 24/25-22
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Nonanoic acid, 4-hydroxy-, gamma-lactone;4-Hydroxynonanoicacid lactone;4-Nonanolide;4-Pentyl-butanolide;4-Pentylbutan-4-olide;5-Pentyldihydro-2(3H)-furanone;Cocos aldehyde;Dihydro-5-pentyl-2(3H)-furanone;Nonan-1,4-olide;Prunolide;g-Amyl-g-butyrolactone;g-Amylbutyrolactone;gamma-Pentyl-gamma-butyrolactone;gamma-N-Amylbutyrolactone;
PSA 26.30000
LogP 2.27230

Synthetic route

: 2430-73-1
nonane-1,4-diol

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
	98%
Electrolysis;	96%
With silica gel; sodium hydrogencarbonate; sodium bromide; 4-hydroxy-TEMPO benzoate In water at 20℃; Electrochemical reaction;	91%
Cp*RuCl(Ph2P(CH2)2NH2-κ2-P,N); potassium tert-butylate In acetone at 30℃; for 1h;	96 % Spectr.

: 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-nonanoic acid methyl ester

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With hydroxide; dihydrogen peroxide	95%

: 292638-85-8
acrylic acid methyl ester

: 111-27-3
hexan-1-ol

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
Stage #1: acrylic acid methyl ester; hexan-1-ol With Quinuclidine; 2,2-bis(4-(trifluoromethyl)phenyl)-1,3,2λ4-oxazaborolidine; Ir[dF(CF3)ppy]2(4,4′-di-tert-butyl-2,2′-bipyridine)PF6 In acetonitrile at 25 - 33℃; for 14h; Irradiation; Sealed tube; Inert atmosphere; Stage #2: In acetonitrile at 50℃; for 3h; regioselective reaction;	90%
With Quinuclidine; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; tetrabutylammonium dihydrogen phosphate In acetonitrile at 27℃; Kinetics; Catalytic behavior; Reagent/catalyst; Irradiation;	84%
With di-tert-butyl peroxide; zinc dibromide In water at 180℃; for 12h; Solvent; Time; Dean-Stark;	70.1%
With di-tert-butyl peroxide at 140 - 170℃; Large scale;	1465 kg
With di-tert-butyl peroxide at 20 - 170℃;	146 g

: 79-10-7
acrylic acid

: 111-27-3
hexan-1-ol

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With di-tert-butyl peroxide at 10 - 160℃;	86.2%
With di-tert-butyl peroxide; zinc dibromide at 180℃; for 12h; Dean-Stark;	76%

: 66-25-1
hexanal

: 292638-85-8
acrylic acid methyl ester

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With chloro-trimethyl-silane; tetraethylammonium tosylate In N,N-dimethyl-formamide Ambient temperature; electroreductive crossed hydrocoupling;	86%

: 33566-57-3
methyl 4-oxononanoate

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With sodium tetrahydroborate; disodium hydrogenphosphate In methanol for 5h; Ambient temperature;	85%

: 120040-75-7
γ-(1-Iodo-n-pentyl)-γ-butyrolactone

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With hydrogen; nickel In ethanol for 24h;	85%

: 2160-89-6
1,1,1,3,3,3-hexafluoroisopropyl acrylate

: 111-27-3
hexan-1-ol

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With quinuclidin-3-yl benzenesulfonate; 3,3,3',3'-tetrakis(trifluoromethyl)-1,1'(3H,3'H)-spirobi<2,1-benzoxasilole>; C36H16F16IrN4(1+)*F6P(1-) In acetonitrile at 20℃; for 14h; Glovebox; Inert atmosphere; Sealed tube; Irradiation;	82%

: 592-76-7
1-Heptene

: 73927-91-0
tributylstannyl iodoacetate

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
2,2'-azobis(isobutyronitrile) In benzene for 8h; Heating;	75%

: 57-57-8
β-Propiolactone

: 66-25-1
hexanal

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
nickel(II) iodide; samarium diiodide In tetrahydrofuran for 1h; Addition;	75%

: 76543-09-4
methyl 3-(oxiran-2-yl)propanoate

: 693-04-9
butyl magnesium bromide

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
Stage #1: butyl magnesium bromide With copper(I) cyanide In tetrahydrofuran at 0℃; for 0.416667h; Inert atmosphere; Stage #2: methyl 3-(oxiran-2-yl)propanoate In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; diethyl ether; water	72%

: 592-76-7
1-Heptene

: 79-08-3
bromoacetic acid

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With dibenzoyl peroxide In benzene Heating;	69%

: 35349-81-6
(E)-3-octene-1,1-dicarboxylic acid

A: 35329-50-1
(E)-4-nonenoic acid

B: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
at 150 - 160℃;	A 64% B n/a

: 91712-77-5
dihydro-5-(4-iodobutyl)-2(3H)-furanone

dilithium cyanodimethylcuprate: dilithium cyanodimethylcuprate

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
In tetrahydrofuran for 2h; Ambient temperature;	61%

: 66-25-1
hexanal

: 140-88-5
ethyl acrylate

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 0℃; for 10h;	57%
With samarium diiodide; tert-butyl alcohol In tetrahydrofuran for 3h; Ambient temperature;	28%

: 66-25-1
hexanal

: 140-88-5
ethyl acrylate

A: 57753-68-1
ethyl γ-hydroxypelargonate

B: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With borax; ethylenediaminetetraacetic acid; bis(dibutylethyl)hexamethylenediammonium hydroxide; triethylamine In water at 20℃; pH=10; Reagent/catalyst; Solvent; Temperature; Concentration; Electrochemical reaction;	A 48% B 23.7%

...Expand

: 37651-49-3
diethyl-(2-methoxycarbonyl-ethyl)-methyl-ammonium; iodide

: 66-25-1
hexanal

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With tetraethylammonium tosylate In N,N-dimethyl-formamide cathodic reduction;	47%

: 111861-22-4
5-(2-Hydroxy-heptyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
at 150 - 160℃; for 0.5h;	41%

: 150171-98-5
(E)-non-3-enenitrile

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With sulfuric acid

: 28163-88-4
(E)-non-3-enoic acid

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With sulfuric acid

: 70478-77-2
7-hydroxynonanoic acid

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With sulfuric acid

: 37056-01-2
4,7-dioxo-nonanoic acid

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With hydrogenchloride; amalgamated zinc; toluene

: 35349-81-6
(E)-3-octene-1,1-dicarboxylic acid

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With sulfuric acid In water for 10h; Heating;

: 127839-79-6
4-Hydroxy-nonanethioic acid benzylamide

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With hydrogenchloride; methyl iodide 1.) THF, RT, 2.) 100 deg C, 3 h; Yield given. Multistep reaction;

: 139398-43-9
4-hydroxy-2-nonenoic acid

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 2068.59 Torr; for 15h; Hydrogenation; lactonization;

(+-)-2,2,4-trichloro-nonanoic acid ethyl ester: (+-)-2,2,4-trichloro-nonanoic acid ethyl ester

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With potassium hydroxide; nickel Hydrogenation.anschliessendes Ansaeuern mit wss. Schwefelsaeure;

: 996-82-7
sodium diethylmalonate

(+-)-1,2-epoxy-heptane: (+-)-1,2-epoxy-heptane

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With ethanol; alkaline solution Erhitzen des Reaktionsprodukts unter vermindertem Druck;

: 37174-92-8
4-oxo-nonanoic acid ethyl ester

A: 6064-52-4
4-oxononanoic acid

B: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
With D-glucose; C. boidinii In phosphate buffer at 20℃; pH=6.0;	A 91 % Chromat. B 4 % Chromat.

: 850480-50-1
4-hydroxynon-2-enal

: 104-61-0
γ-nonalactone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 25 percent / sodium chlorite; 1 mM HCl; sulfamic acid / H2O / 3 h / 20 °C 2: hydrogen / Pd/C / methanol / 15 h / 2068.59 Torr View Scheme

: 104-61-0
γ-nonalactone

: 75-04-7
ethylamine

: N-ethyl-4-hydroxynonanamide

Conditions

Conditions	Yield
at 50℃; for 24h;	98%

: 104-61-0
γ-nonalactone

: 57788-65-5
4-hydroxynonanamide

Conditions

Conditions	Yield
With ammonia at 50 - 60℃; for 168h;	94%

: 104-61-0
γ-nonalactone

: 133287-30-6
(S)-2-amino-3-phenyl-N-[(R)-1-phenylethyl]propanamide

: 1219498-04-0
(S)-2-[4-hydroxynonanamide]-3-phenyl-N-[(R)-1-phenylethyl]propanamide

Conditions

Conditions	Yield
Stage #1: (S)-2-amino-3-phenyl-N-[(R)-1-phenylethyl]propanamide With trimethylaluminum In dichloromethane; toluene at 0℃; for 1h; Stage #2: γ-nonalactone In dichloromethane; toluene at 20℃;	93%

: 104-61-0
γ-nonalactone

: 2430-73-1
nonane-1,4-diol

Conditions

Conditions	Yield
With hydrogen; sodium methylate; RuCl2(L-1) In tetrahydrofuran at 100℃; under 37503.8 Torr; for 2.5h; Product distribution / selectivity;	91%
With potassium methanolate; hydrogen; homogeneous ruthenium complex In toluene at 100℃; under 37503.8 Torr; for 4h;	91%
With C15H29MnNO3P2(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 110℃; under 22502.3 Torr; for 24h; Inert atmosphere; Autoclave;	82%

: 104-61-0
γ-nonalactone

: 74-89-5
methylamine

: 57753-57-8
N-methyl-4-hydroxynonanamide

Conditions

Conditions	Yield
In tetrahydrofuran at 65℃; for 168h;	89%

: 104-61-0
γ-nonalactone

: 5-pentyl-dihydro-furan-2-thione

Conditions

Conditions	Yield
With Lawessons reagent; Hexamethyldisiloxane at 120℃; for 0.0416667h; microwave irradiation;	89%

: 104-61-0
γ-nonalactone

: 75-26-3
isopropyl bromide

: 118438-05-4
isopropyl 4-hydroxynonanoate

Conditions

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	83%
Stage #1: γ-nonalactone With potassium hydroxide In methanol at 20℃; for 72h; Stage #2: isopropyl bromide In dimethyl sulfoxide at 20℃; for 20h;	4.62 g

: 925-90-6
ethylmagnesium bromide

: 104-61-0
γ-nonalactone

: C11H22O2

Conditions

Conditions	Yield
With titanium(IV) isopropylate; methylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1.5h; Inert atmosphere;	74%

: 760-32-7
diethylmethylsilane

: 201230-82-2
carbon monoxide

: 104-61-0
γ-nonalactone

A: 5290-28-8
diethylmethylsilyl acetate

B: 104665-10-3
5-<<(diethylmethylsilyl)oxy>-methylene>nonanoic acid diethylmethylsilyl ester

Conditions

Conditions	Yield
With pyridine; dicobalt octacarbonyl In benzene at 140℃; for 6h;	A n/a B 73%

...Expand

: 760-32-7
diethylmethylsilane

: 201230-82-2
carbon monoxide

: 104-61-0
γ-nonalactone

: 104665-10-3
5-<<(diethylmethylsilyl)oxy>-methylene>nonanoic acid diethylmethylsilyl ester

Conditions

Conditions	Yield
With pyridine; dicobalt octacarbonyl In benzene at 140℃; under 38000 Torr; for 6h;	73%

...Expand

: 3288-80-0
N,N,N-trimethylhydrazinium iodide

: 104-61-0
γ-nonalactone

: C12H26N2O2

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol at 50℃; for 5h;	63%

: 104-61-0
γ-nonalactone

: 40657-54-3
dec-5-en-2-one

Conditions

Conditions	Yield
With acetic acid at 450℃;	52%

: 50-00-0
formaldehyd

: 109-79-5
1-butanethiol

: 104-61-0
γ-nonalactone

A: 120388-37-6
5-amyl-5-butylthiotetrahydrofuran-2-one

B: 120388-36-5
5-amyl-3-butylthiomethylenfuran-2-one

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 45 - 55℃; for 7h;	A 18% B 51%

...Expand

: 104-61-0
γ-nonalactone

: 142-62-1
hexanoic acid

A: 927-49-1
dipentyl ketone

B: (9E)-tetradec-9-en-6-one

Conditions

Conditions	Yield
pumice; zinc diacetate; manganese(II) acetate at 450℃;	A 50% B 5%

...Expand

gamma-Nonanolactone Consensus Reports

COCONUT ALDEHYDE(104-61-0) is reported in EPA TSCA Inventory.

gamma-Nonanolactone Specification

The CAS registry number of gamma-Nonanolactone is 104-61-0. Its EINECS registry number is 203-219-1. The IUPAC name is 5-pentyloxolan-2-one. In addition, the molecular formula is C₉H₁₆O₂ and the molecular weight is 156.22. It is also called 2(3H)-furanone, dihydro-5-pentyl-. What's more, it belongs to the classes of Carbonyl Compounds; Organic Building Blocks; Lactone Flavors. It should be stored in a cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 1.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.85; (4)ACD/LogD (pH 7.4): 1.85; (5)ACD/BCF (pH 5.5): 15.08; (6)ACD/BCF (pH 7.4): 15.08; (7)ACD/KOC (pH 5.5): 242.74; (8)ACD/KOC (pH 7.4): 242.74; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.444; (14)Molar Refractivity: 43.4 cm³; (15)Molar Volume: 163.3 cm³; (16)Polarizability: 17.2 ×10^-24cm³; (17)Surface Tension: 30.6 dyne/cm; (18)Density: 0.956 g/cm³; (19)Flash Point: 98.8 °C; (20)Enthalpy of Vaporization: 50.45 kJ/mol; (21)Boiling Point: 266.6 °C at 760 mmHg; (22)Vapour Pressure: 0.00858 mmHg at 25°C.

Preparation of gamma-Nonanolactone: it can be prepared by nonenoic acid through esterification reaction. And then after a series of extraction, washing and distillation you can get the desired product. In addition, it can be prepared by g-Keto-methylnonanoat. This reaction will need reagents NaBH₄ and Na₂HPO₄*12H₂O, and solvent methanol. The reaction time is 5 hours with ambient temperature. The yield is about 85%.

gamma-Nonanolactone can be prepared by g-Keto-methylnonanoat

Uses of gamma-Nonanolactone: it is used in the preparation of food flavors and feed flavors. In addition, it can react with methylamine to get 4-hydroxy-nonanoic acid methylamide. This reaction needs solvent tetrahydrofuran. The reaction time is 7 days at reaction temperature of 65 °C. The yield is about 89%.

gamma-Nonanolactone can react with methylamine to get 4-hydroxy-nonanoic acid methylamide.

When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes. In addition, do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1OC(CCCCC)CC1
(2)InChI: InChI=1/C9H16O2/c1-2-3-4-5-8-6-7-9(10)11-8/h8H,2-7H2,1H3
(3)InChIKey: OALYTRUKMRCXNH-UHFFFAOYAG

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	oral	3440mg/kg (3440mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 889, 1975.
rat	LD50	oral	6600mg/kg (6600mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 889, 1975.

Product Name

gamma-Nonanolactone

Synthetic route

gamma-Nonanolactone Consensus Reports

gamma-Nonanolactone Specification

Related Products

Hot Products