Gamma-undecalactone

Base Information

• Chemical Name: Gamma-undecalactone
• CAS No.: 104-67-6
• Deprecated CAS: 57084-17-0,176201-25-5
• Molecular Formula: C11H20O2
• Molecular Weight: 184.279
• Hs Code.: 29322090
• European Community (EC) Number: 203-225-4
• NSC Number: 406421,76413,46118
• UNII: QB1T0AG2YL
• DSSTox Substance ID: DTXSID4034287
• Nikkaji Number: J1.182G
• Wikidata: Q24734376
• RXCUI: 1376148
• Metabolomics Workbench ID: 4364
• ChEMBL ID: CHEMBL195827
• Mol file: 104-67-6.mol

Synonyms:Gamma-undecalactone;104-67-6;5-Heptyldihydrofuran-2(3H)-one;4-Undecanolide;Undecanoic gamma-lactone;2(3H)-Furanone, 5-heptyldihydro-;Undecan-4-olide;Peach aldehyde;Persicol;1,4-Undecanolide;Peach lactone;5-heptyloxolan-2-one;Aldehyde C-14 peach;gamma-Undecanolactone;5-Heptyldihydro-2(3H)-furanone;gamma-Undecanolide;4-Hydroxyundecanoic acid lactone;1,4-Hendecanolide;.gamma.-Undecalactone;FEMA No. 3091;gamma-n-Heptylbutyrolactone;gamma-Undekalakton;gamma-Undekalakton [Czech];.gamma.-n-Heptylbutyrolactone;gamma-Undecalactone (natural);NSC 406421;5-Heptyl-dihydro-furan-2-one;.gamma.-Undecalatone;.gamma.-Undecanolide;CCRIS 1425;gamma-Heptyl-gamma-butyrolactone;57084-17-0;xi-gamma-Undecalactone;.gamma.-Undecanolactone;EINECS 203-225-4;UNII-QB1T0AG2YL;MFCD00005405;QB1T0AG2YL;.gamma.-Heptylbutyrolactone;BRN 0081943;AI3-00751;CHEMBL195827;Undecanoic acid, 4-hydroxy-, gamma-lactone;DTXSID4034287;CHEBI:89362;5-Heptyl-dihydrofuran-2(3H)-one;Dihydro-5-heptyl-2(3H)-furanone;.gamma.-Heptyl-.gamma.-butyrolactone;NSC-46118;NSC-76413;NSC-406421;4-Hydroxyundecanoic acid, .gamma.-lactone;Undecanoic acid, 4-hydroxy-, .gamma.-lactone;EC 203-225-4;WLN: T5OVTJ E7;Undecanoic acid, .gamma.-lactone;Peche Pure;undecan-4-olid;Undecanolide-1,4;.gamma.-Undekalakton;Undecan- 4- olide;Undecanoic ?-lactone;undecan - 4 - olide;undecylene methyl lactone;Undecanoic gamma -lactone;GAMMA UNDECALACTONE;UNDECALACTONE GAMMA;Undecanoic .gamma.-lactone;5-Heptyltetrahydro-2-furanone;SCHEMBL113498;Undecanoic gamma-lactone, 99%;DTXCID2014287;Neutralizing agent 350120-1;PHXATPHONSXBIL-UHFFFAOYSA-;4- hydroxyundecanoic acid lactone;GAMMA-UNDECALACTONE [FCC];GAMMA-UNDECALACTONE [INCI];HMS1786B22;(RS)-.GAMMA.-UNDECALACTONE;2(3h)-furanona, 5-heptildihidro-;NSC46118;NSC76413;5-Heptyldihydro-2(3H)-furanone #;Tox21_300063;BDBM50168011;LMFA07040030;NSC 46118;NSC 76413;NSC406421;.GAMMA.-UNDECALACTONE [FHFI];AKOS001076126;(+/-)-.GAMMA.-UNDECALACTONE;CS-W016994;HY-W016278;LS-2358;gamma-Undecalactone, analytical standard;gamma-Undecalactone, >=98%, FCC, FG;NCGC00164025-01;NCGC00164025-02;NCGC00254148-01;BS-14211;CAS-104-67-6;SY011229;FT-0626626;FT-0695781;U0003;EN300-05986;D70490;gamma-Undecalactone, natural (US), >=98%, FG;(4-FLUORO-PHENYL)-PHOSPHONICACIDDIETHYLESTER;J-001223;Q24734376;Z90120148

Chemical Property of Gamma-undecalactone

Chemical Property:

• Appearance/Colour: Colourless oily liquid
• Vapor Pressure: 0.00271mmHg at 25°C
• Melting Point: 164～166℃
• Refractive Index: n20/D 1.451
• Boiling Point: 286 °C at 760 mmHg
• Flash Point: 112.7 °C
• PSA: 26.30000
• Density: 0.9425 g/cm³
• LogP: 3.05250
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Insoluble in water
• Water Solubility.: 158mg/L at 20℃
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 184.146329876
• Heavy Atom Count: 13
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

4-Undecanolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-52/53
• Safety Statements: 26-36-37/39-36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Lactones
• Canonical SMILES: CCCCCCCC1CCC(=O)O1
• Description: GAMMA-UNDECALACTONE? is a flavoring ingredient. It is industrially important flavor compounds that are widely distributed in foods, fruits, and beverages and are used in many fruity aromatic foods and cosmetics. It is often used in peach, apricot, pear, maple, coconut, tropical, butterscotch, grenadine and date flavors. It is also a volatile flavor constituent found in low-fat ice cream.
• Uses: Traditionally, the bark and leaves of the peach tree have been used as an anthelmintic, an expectorant, an astringent, and a diuretic, as well as to treat insomnia, cough, and constipation. In the 1970s, peach pits (Laetrile) were a popular but unproved treatment for cancer in other countries. Topically, peach is used to treat minor skin disorders such as burns, abrasions, blisters, scratches, eczema, psoriasis, and warts. 4-Undecanolide is used in the study of primary mutagenicity screening of food additives used in Japan.

Technology Process of Gamma-undecalactone

There total 43 articles about Gamma-undecalactone 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: 94.0%

10-undecenoic acid (112-38-9) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Guidance literature:

With 2Zn⁽²⁺⁾*(CH₃)3NC₂H₄OH⁽¹⁺⁾*5Cl^(1-)=[HOC₂H₄N(CH₃)3]Zn₂Cl₅; at 130 ℃; for 8h;

DOI:10.1016/j.tetlet.2012.04.112

Reference yield: 90.0%

undec-1-yn-4-ol (22127-86-2) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Guidance literature:

With methanesulfonic acid; C₂₁H₁₂F₉P*C₈H₁₈NO₄S₂^(1-)*Au⁽¹⁺⁾; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 20 ℃; for 5h; Reagent/catalyst;

DOI:10.1021/ol302323a DOI:10.1021/ol302323a

Reference yield: 87.0%

1-(cyclopropylidene)octane (50915-95-2) → 5-heptyldihydro-2(3H)-furanone (104-67-6)

Guidance literature:

With trifluoroacetyl peroxide; In dichloromethane; at 0 ℃; for 6h;

DOI:10.1016/S0040-4020(98)00371-8

upstream raw materials:

(-)-4-hydroxy-undeca-6,8,10-triynoic acid

1,4-undecanediol

4-hydroxyundecanoic acid

methyl 4-oxo-dodecanoate

Downstream raw materials:

undecanoyl chloride

undecylenic acid

1-Decene

(4S)-4-heptyl-γ-butanolide

Refernces

• 1、 Goossen, Lukas J.,Ohlmann, Dominik M.,Dierker, Markus. "Silver triflate-catalysed synthesis of γ-lactones from fatty acids". . p. 197 - 200. Retrieved 2010.
• 2、 Kobayashi, Shu,Miyamura, Hiroyuki,Akiyama, Ryo,Ishida, Tasuku. "Highly active, immobilized ruthenium catalysts for oxidation of alcohols to aldehydes and ketones. Preparation and use in both batch and flow systems". . p. 9251 - 9254. Retrieved 2005.
• 3、 -. "A reaction synthesis and rectification γ - XI lactone with synthetic perfume method (by machine translation)". Paragraph 0040-0056. . Retrieved 2019/01/08.
• 4、 Shu, Chao,Liu, Meng-Qi,Sun, Yu-Zhe,Ye, Long-Wu. "Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation". . p. 4958 - 4961. Retrieved 2013/01/15.