Gamma-nonalactone

Base Information

• Chemical Name: Gamma-nonalactone
• CAS No.: 104-61-0
• Deprecated CAS: 57084-16-9,82373-92-0,82373-92-0
• Molecular Formula: C9H16O2
• Molecular Weight: 156.225
• Hs Code.: 29322090
• European Community (EC) Number: 203-219-1
• NSC Number: 46099,24253
• UNII: I1XGH66S8P
• DSSTox Substance ID: DTXSID0034229
• Nikkaji Number: J2.412K
• Wikipedia: Gamma-Nonalactone
• Wikidata: Q11255995
• RXCUI: 1659905
• Metabolomics Workbench ID: 4355
• ChEMBL ID: CHEMBL191935
• Mol file: 104-61-0.mol

Synonyms:104-61-0;Gamma-nonalactone;gamma-Nonanolactone;5-pentyldihydrofuran-2(3H)-one;5-pentyloxolan-2-one;2(3H)-Furanone, dihydro-5-pentyl-;Prunolide;gamma-Nonanolide;Nonan-1,4-olide;Cocos aldehyde;Coconut aldehyde;4-Nonanolide;1,4-Nonalolide;4-Pentyl-butanolide;Aldehyde C-18;4-Nonalactone;DIHYDRO-5-PENTYL-2(3H)-FURANONE;gamma-Nonylactone;FEMA No. 2781;gamma-Nonyllactone;Nonan-4-olide;gamma-Pelargolactone;1,4-Nonyl lactone;gamma-Nonanoic lactone;delta-n-Amylbutyrolactone;FEMA Number 2781;gamma-N-Amylbutyrolactone;gamma-Amyl-gamma-butyrolactone;.gamma.-Nonalactone;gamma-Pentyl-gamma-butyrolactone;HSDB 5360;rac-gamma-Nonanolactone;EINECS 203-219-1;4-Amyl-4-hydroxybutyric acid lactone;4-Hydroxynonanoic acid, gamma-lactone;UNII-I1XGH66S8P;.gamma.-n-Amylbutyrolactone;I1XGH66S8P;Nonanoic acid, 4-hydroxy-, gamma-lactone;AI3-02457;CHEMBL191935;DTXSID0034229;Dihydro-5-pentylfuran-2(3H)-one;4-Hydroxynonanoic acid gamma-lactone;NSC 24253;NSC 46099;NSC-24253;NSC-46099;apricolin;4-Hydroxynonanoic acid, .gamma.-lactone;EC 203-219-1;82373-92-0;4-Pentylbutanolide;.gamma.-Nonalacton;.gamma.-Nonanolide;Nonan- 4- olide;MFCD00005403;gamma-Pelargonolactone;.gamma.-Nonanolactone;NONYL LACTONE;nonan - 4 - olide;gamma -Nonanoic lactone;(+-)-gamma-Nonalactone;.gamma.-Amylbutyrolactone;.gamma.-Nonanoic lactone;5-Pentyl-.gamma.-lactone;gamma-Nonanoic lactone, 97%;SCHEMBL112484;4-Hydroxynonanoic acid lactone;5-Pentyl-dihydro-furan-2-one;GAMMA-NONALACTONE [FCC];DTXCID8014229;GAMMA-NONALACTONE [INCI];5-pentyl-tetrahydro-furan-2-one;OALYTRUKMRCXNH-UHFFFAOYSA-;(.+/-.)-.gamma.-Nonalactone;5-Pentyldihydro-2(3H)-furanone;Dihydro-5-pentyl-2(3H)-furanon;.gamma.-Amyl-.gamma.-butyrolactone;.GAMMA.-NONALACTONE [FHFI];NSC24253;NSC46099;(3H)-Dihydro-5-pentyl-2-furanone;5-Pentyldihydro-2(3H)-furanone #;Tox21_301039;BBL027520;BDBM50167995;LMFA07040021;STL373781;AKOS015904806;CS-W017997;DS-3247;LS-2984;DELTA-N-AMYLBUTYROLACTONE [HSDB];NCGC00164129-01;NCGC00164129-02;NCGC00254941-01;CAS-104-61-0;gamma-Nonanoic lactone, >=98%, FCC, FG;gamma-Nonanoic lactone, natural, 98%, FG;FT-0686718;N0285;Nonanoic acid, 4-hydroxy-, .gamma.-lactone;D70273;EN300-342288;gamma-Nonalactone, analytical reference material;J-001202;Q11255995;Z1255430984

Chemical Property of Gamma-nonalactone

Chemical Property:

• Vapor Pressure: 0.00858mmHg at 25°C
• Refractive Index: n20/D 1.447(lit.)
• Boiling Point: 266.6 °C at 760 mmHg
• Flash Point: 98.8 °C
• PSA: 26.30000
• Density: 0.956 g/cm³
• LogP: 2.27230
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Sparingly), Hexanes (Slightly)
• Water Solubility.: 9.22g/L(25 oC)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 156.115029749
• Heavy Atom Count: 11
• Complexity: 132

Purity/Quality:

98% ^*data from raw suppliers

rac-γ-Nonanolactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Lactones
• Canonical SMILES: CCCCCC1CCC(=O)O1
• Description: 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 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.
• Uses: (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. 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. (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.

Technology Process of Gamma-nonalactone

There total 45 articles about Gamma-nonalactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

nonane-1,4-diol (2430-73-1) → γ-nonalactone (104-61-0,57084-16-9)

Guidance literature:

Reference yield: 95.0%

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-nonanoic acid methyl ester → γ-nonalactone (104-61-0,57084-16-9)

Guidance literature:

With hydroxide; dihydrogen peroxide;

DOI:10.1016/0040-4039(95)00148-6

Reference yield: 90.0%

acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) + hexan-1-ol (111-27-3) → γ-nonalactone (104-61-0,57084-16-9)

Guidance literature:

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;

In acetonitrile; at 50 ℃; for 3h; regioselective reaction;

DOI:10.1055/s-0040-1707114

upstream raw materials:

(E)-non-3-enenitrile

(E)-non-3-enoic acid

7-hydroxynonanoic acid

4,7-dioxo-nonanoic acid

Downstream raw materials:

2-methyldecane-2,5-diol

(R)-(+)-γ-nonalactone

(S)-4-Hydroxy-nonanoic acid

nonanoic acid

Refernces

• 1、 Alary, Jacques,Bravais, Fabienne,Cravedi, Jean-Pierre,Debrauwer, Laurent,Rao, Dinesh,Bories, Georges. "Mercapturic Acid Conjugates as Urinary End Metabolites of the Lipid Peroxidation Product 4-Hydroxy-2-nonenal in the Rat". . p. 34 - 39. Retrieved 1995.
• 2、 Tu, Song,Shen, Youyu,Dong, Wan,Yang, Jing,Zhang, Chen,Ye, Liyi. "Efficient and convenient preparation of γ-nonalactone, with use of a Dean-Stark trap to remove methanol". . p. 1613 - 1618. Retrieved 2014.
• 3、 Machrouhi, Fouzia,Namy, Jean-Louis. "A new coupling reaction between β-lactones and electrophiles mediated by a SmI2/(NiI2 catalytic) system". . p. 11111 - 11122. Retrieved 1998.
• 4、 Miyano, Sotaro,Hokari, Hiroshi,Umeda, Yoshiharu,Hashimoto, Harukichi. "Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C1 Unit. II. The Preparation and Synthetic Application of 1-Chloro-3-iodoheptane". . p. 770 - 774. Retrieved 1980.
• 5、 Ugurchieva,Lozanova,Zlokazov,Veselovsky. "Synthesis of (±)-4-alkanolides from pent-4-enoic acid". . p. 657 - 659. Retrieved 2008.
• 6、 -. "Preparation method of coconut aldehyde". Paragraph 0017-0022. . Retrieved 2021/02/10.
• 7、 Sakai, Kentaro,Oisaki, Kounosuke,Kanai, Motomu. "Identification of Bond-Weakening Spirosilane Catalyst for Photoredox α-C?H Alkylation of Alcohols". supporting information. p. 337 - 343. Retrieved 2019/12/24.