104-61-0

Basic information

• Product Name: gamma-Nonanolactone
• Synonyms: (±)-4-n-Pentylbutyrolactone;(R,S)-5-Pentyl-dihydro-furan-2-one;(RS)-γ-Nonalactone;.gamma.-Amylbutyrolactone;1,4-Nonalolide;1,4-nonanolactone;2(3H)-Furanone,dihydro-5-pentyl-;4-Hydroxynonanoic acid lactone
• CAS NO: 104-61-0
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22
• EINECS: 203-219-1
• Product Categories: Carbonyl Compounds;Lactones;Organic Building Blocks;lactone flavors;Cosmetics;Food Additive
• Mol File: 104-61-0.mol
• Article Data: 46

Chemical Properties

• Boiling Point: 121-122 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.976 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00858mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Sparingly), Hexanes (Slightly)
• Water Solubility: 9.22g/L(25 oC)
• Stability: Hygroscopic
• CAS DataBase Reference: gamma-Nonanolactone(CAS DataBase Reference)
• NIST Chemistry Reference: gamma-Nonanolactone(104-61-0)
• EPA Substance Registry System: gamma-Nonanolactone(104-61-0)

Safety Data

• Safety Statements: 24/25-22
• WGK Germany: 1
• RTECS: LU3675000
• Hazardous Substances Data: 104-61-0(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 104-61-0 differently. You can refer to the following data:
1. Gamma-Nonalactone (5-Pentyloxolan-2-one) is a colorless to pale yellow clear oily liquid. It is found in bourbon whiskey, black currant berries, melon, papaya, pineapple, fresh blackberry, etc.1,2 It has a creamy and coconut-like odor.3 It is used as a flavoring agent in food to give coconut flavor. It is also a potential multi-species attractant lure for grain beetle pests.4
2. γ-Nonalactone has a strong odor reminiscent of coconut and a fatty, peculiar taste. May be synthesized by reacting methylacry- late and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid; by lactonizα- tion of nonenoic acid.

Reference

https://en.wikipedia.org/wiki/Gamma-Nonalactone George A. Burdock, Encyclopedia of Food and Color Additives, Band 1, 1996, ISBN 0-8493-9416-3 http://www.thegoodscentscompany.com https://www.sigmaaldrich.com

Chemical Properties

Different sources of media describe the Chemical Properties of 104-61-0 differently. You can refer to the following data:
1. γ-Nonalactone has a strong odor reminiscent of coconut and a fatty, peculiar taste.
2. gamma-Nonanolactone occurs in many foods and is a pale yellow liquidwith a coconut-like aroma. It has numerous applications, similarly to those of ??-octalactone, in aroma compositions and perfumery.

Occurrence

Reported found in peaches, apricots, roasted barely, rum, tomato, currants, guava, raisin, papaya, peach, pineapple, blackberry, strawberry jam, asparagus, wheat and crispbread, Camembert cheese, butter, milk, chicken, beef, lamb and pork fat, cooked beef and pork, beer, cognac, whiskies, sherry, grape wines, cocoa, green tea, pecan, oats, soybean, avocado, passion fruit, plum, plumcot, beans, mushroom, starfruit, fenugreek, mango, tamarind, rice, prickly pear, buckwheat, licorice, malt, wort, cherimoya, Bourbon vanilla, shrimp, nectarine, maté and sweet grass oil.

Uses

Different sources of media describe the Uses of 104-61-0 differently. You can refer to the following data:
1. (γ-Nonalactone is one of the prominent, odour active compounds present in freshly cooked rice, and also has a coconut-like scent. γ-Nonalactone is also present in aging beers and other fermenting products.
2. In flavor applications, this compound contributes to caramel notes. In fragrance applications, this compound contributes is used in amber, balsam, floral, juniper berry, nutmeg, pine, coconut, maple and oriental notes.
3. (Gamma)-Nonalactone is a synthetic flavoring agent that is a colorless to yellow liquid of strong, coconut-like odor. It is soluble in most fixed oils, mineral oil, and propylene glycol. It is stable in acids and unstable in alkali and should be stored in glass, tin, or aluminum containers. It is used in coconut flavors and has application in gelatins, puddings, baked goods, candy, and ice cream at 11–55 ppm. It is also termed aldehyde c-18.

Preparation

By reacting methylacrylate and hexanol in the presence of ditertiarybutyl peroxide; by condensation of undecylenic acid and malonic acid by lactonization of nonenoic acid

Aroma threshold values

Detection: 7 ppb

Taste threshold values

Taste characteristics at 10 ppm: coconut, creamy, waxy with fatty milky notes

General Description

γ-Nonanoic lactone is an oak lactone commonly found in wines aged in oak barrels. It is the main flavor component of coconut. γ-Nonanoic lactone is also a potential multi-species attractant lure for grain beetle pests.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

InChI:InChI=1/C9H16O2/c1-2-3-4-5-8-6-7-9(10)11-8/h8H,2-7H2,1H3/t8-/m0/s1

Synthetic route

nonane-1,4-diol (2430-73-1) → γ-nonalactone (104-61-0)

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 → γ-nonalactone (104-61-0)

Conditions	Yield
With hydroxide; dihydrogen peroxide	95%

acrylic acid methyl ester (292638-85-8) + hexan-1-ol (111-27-3) → γ-nonalactone (104-61-0)

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

acrylic acid (79-10-7) + hexan-1-ol (111-27-3) → γ-nonalactone (104-61-0)

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%

hexanal (66-25-1) + acrylic acid methyl ester (292638-85-8) → γ-nonalactone (104-61-0)

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

methyl 4-oxononanoate (33566-57-3) → γ-nonalactone (104-61-0)

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

γ-(1-Iodo-n-pentyl)-γ-butyrolactone (120040-75-7) → γ-nonalactone (104-61-0)

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

1,1,1,3,3,3-hexafluoroisopropyl acrylate (2160-89-6) + hexan-1-ol (111-27-3) → γ-nonalactone (104-61-0)

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%

1-Heptene (592-76-7) + tributylstannyl iodoacetate (73927-91-0) → γ-nonalactone (104-61-0)

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

β-Propiolactone (57-57-8) + hexanal (66-25-1) → γ-nonalactone (104-61-0)

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

methyl 3-(oxiran-2-yl)propanoate (76543-09-4) + butyl magnesium bromide (693-04-9) → γ-nonalactone (104-61-0)

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%

1-Heptene (592-76-7) + bromoacetic acid (79-08-3) → γ-nonalactone (104-61-0)

Conditions	Yield
With dibenzoyl peroxide In benzene Heating;	69%

(E)-3-octene-1,1-dicarboxylic acid (35349-81-6) → (E)-4-nonenoic acid (35329-50-1) + γ-nonalactone (104-61-0)

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

dihydro-5-(4-iodobutyl)-2(3H)-furanone (91712-77-5) + dilithium cyanodimethylcuprate → γ-nonalactone (104-61-0)

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

hexanal (66-25-1) + ethyl acrylate (140-88-5) → γ-nonalactone (104-61-0)

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%

hexanal (66-25-1) + ethyl acrylate (140-88-5) → ethyl γ-hydroxypelargonate (57753-68-1) + γ-nonalactone (104-61-0)

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%

diethyl-(2-methoxycarbonyl-ethyl)-methyl-ammonium; iodide (37651-49-3) + hexanal (66-25-1) → γ-nonalactone (104-61-0)

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

5-(2-Hydroxy-heptyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione (111861-22-4) → γ-nonalactone (104-61-0)

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

(E)-non-3-enenitrile (150171-98-5) → γ-nonalactone (104-61-0)

Conditions	Yield
With sulfuric acid

(E)-non-3-enoic acid (28163-88-4) → γ-nonalactone (104-61-0)

Conditions	Yield
With sulfuric acid

7-hydroxynonanoic acid (70478-77-2) → γ-nonalactone (104-61-0)

Conditions	Yield
With sulfuric acid

4,7-dioxo-nonanoic acid (37056-01-2) → γ-nonalactone (104-61-0)

Conditions	Yield
With hydrogenchloride; amalgamated zinc; toluene

(E)-3-octene-1,1-dicarboxylic acid (35349-81-6) → γ-nonalactone (104-61-0)

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

4-Hydroxy-nonanethioic acid benzylamide (127839-79-6) → γ-nonalactone (104-61-0)

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

4-hydroxy-2-nonenoic acid (139398-43-9) → γ-nonalactone (104-61-0)

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 → γ-nonalactone (104-61-0)

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

sodium diethylmalonate (996-82-7) + (+-)-1,2-epoxy-heptane → γ-nonalactone (104-61-0)

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

4-oxo-nonanoic acid ethyl ester (37174-92-8) → 4-oxononanoic acid (6064-52-4) + γ-nonalactone (104-61-0)

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

4-hydroxynon-2-enal (850480-50-1) → γ-nonalactone (104-61-0)

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

γ-nonalactone (104-61-0) + ethylamine (75-04-7) → N-ethyl-4-hydroxynonanamide

Conditions	Yield
at 50℃; for 24h;	98%

γ-nonalactone (104-61-0) → 4-hydroxynonanamide (57788-65-5)

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

γ-nonalactone (104-61-0) + (S)-2-amino-3-phenyl-N-[(R)-1-phenylethyl]propanamide (133287-30-6) → (S)-2-[4-hydroxynonanamide]-3-phenyl-N-[(R)-1-phenylethyl]propanamide (1219498-04-0)

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%

γ-nonalactone (104-61-0) → nonane-1,4-diol (2430-73-1)

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%

γ-nonalactone (104-61-0) + methylamine (74-89-5) → N-methyl-4-hydroxynonanamide (57753-57-8)

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

γ-nonalactone (104-61-0) → 5-pentyl-dihydro-furan-2-thione

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

γ-nonalactone (104-61-0) + isopropyl bromide (75-26-3) → isopropyl 4-hydroxynonanoate (118438-05-4)

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

ethylmagnesium bromide (925-90-6) + γ-nonalactone (104-61-0) → C11H22O2

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

diethylmethylsilane (760-32-7) + carbon monoxide (201230-82-2) + γ-nonalactone (104-61-0) → diethylmethylsilyl acetate (5290-28-8) + 5-<<(diethylmethylsilyl)oxy>-methylene>nonanoic acid diethylmethylsilyl ester (104665-10-3)

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

diethylmethylsilane (760-32-7) + carbon monoxide (201230-82-2) + γ-nonalactone (104-61-0) → 5-<<(diethylmethylsilyl)oxy>-methylene>nonanoic acid diethylmethylsilyl ester (104665-10-3)

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

N,N,N-trimethylhydrazinium iodide (3288-80-0) + γ-nonalactone (104-61-0) → C12H26N2O2

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

γ-nonalactone (104-61-0) → dec-5-en-2-one (40657-54-3)

Conditions	Yield
With acetic acid at 450℃;	52%

formaldehyd (50-00-0) + 1-butanethiol (109-79-5) + γ-nonalactone (104-61-0) → 5-amyl-5-butylthiotetrahydrofuran-2-one (120388-37-6) + 5-amyl-3-butylthiomethylenfuran-2-one (120388-36-5)

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

γ-nonalactone (104-61-0) + hexanoic acid (142-62-1) → dipentyl ketone (927-49-1) + (9E)-tetradec-9-en-6-one

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

Upstream product

• 19513-05-4 Manganese triacetate dihydrate 
• 121-44-8 Triethylamine 
• 592-76-7 1-HEPTENE 
• 29830-11-3 nonenoic acid 
• 96-33-3 Methyl acrylate 

Downstream Products

• 1046116-27-1 AMbrisentan-d10 
• 1046118-40-4 Atorvastatin Lactone Diepoxide 
• 1046118-44-8 Dihydroxy Diketo Atorvastatin IMpurity 
• 1046118-65-3 5-(3-BROMO-4-FLUOROPHENYL)IMIDAZOLIDINE-2,4-DIONE 
• 1046119-63-4 N-[Methyl[1-[6-(trifluoroMethyl)-3-pyridinyl]ethyl]-λ4-sulfanylidene]cyanaMide 
• 1046121-01-0 6-ethyl-5H-pyrrolo[3,4-b]pyridin-7(6H)-one 
• 104612-30-8 5-Quinolinecarboxamide,6-hydroxy-(9CI) 
• 104612-35-3 (S)-(-)-2-HYDROXY-N-METHYLSUCCINIMIDE 
• 104612-36-4 5-Bromo-2-hydroxynicotinic acid 
• 104613-43-6 N-m-Tolyl-N-phenylhydroxylamine 
• 104613-44-7 versicolactone B 
• 1046-13-5 2-(butylsulfanyl)-3-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 104613-64-1 2-AMINO-4-CHLORO-5-METHYLBENZENESULFONYL CHLORIDE 
• 104613-70-9 [(2-Hydroxyphenyl)[(phenylmethyl)amino]methyl]phosphonic acid hydrogen butyl ester 

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• 37056-01-2  4,7-dioxo-nonanoic acid 
• 996-82-7  sodium diethylmalonate 
• 91712-77-5  dihydro-5-(4-iodobutyl)-2(3H)-furanone 
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• 63357-96-0  (R)-(+)-γ-nonalactone 
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