Undecan-4-olide

Undecan-4-olide Basic information
Description References
Product Name:Undecan-4-olide
Synonyms:GAMMA-UNDECANOLACTONE;GAMMA-HEPTYL-GAMMA-BUTYROLACTONE;G-N-HEPTYLBUTYROLACTONE;G-UNDECALACTONE;1,4-UNDECANOLIDE;UNDECALACTONE, GAMMA;UNDECAN-4-OLIDE;UNDECANOIC GAMMA-LACTONE
CAS:104-67-6
MF:C11H20O2
MW:184.28
EINECS:203-225-4
Product Categories:Food Additive;Cosmetics;Bioactive Small Molecules;Building Blocks;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Lactones;Organic Building Blocks;U
Mol File:104-67-6.mol
Undecan-4-olide Structure
Undecan-4-olide Chemical Properties
Melting point 164~166℃
Boiling point 164-166 °C/13 mmHg (lit.)
density 0.949 g/mL at 25 °C (lit.)
vapor pressure 0.274Pa at 25℃
refractive index n20/D 1.451
FEMA 3091 | GAMMA-UNDECALACTONE
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility Insoluble in water
form Liquid
Specific Gravity0.944 (20/4℃)
color Clear colorless
Odorat 100.00 %. fruity peach creamy fatty lactonic apricot ketonic coconut
Odor Typefruity
Water Solubility 158mg/L at 20℃
JECFA Number233
BRN 81943
LogP3.6 at 25℃
CAS DataBase Reference104-67-6(CAS DataBase Reference)
NIST Chemistry Reference2(3H)-Furanone, 5-heptyldihydro-(104-67-6)
EPA Substance Registry System5-Heptyldihydro-2(3H)-furanone (104-67-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-52/53
Safety Statements 26-36-37/39-36/37-24/25
WGK Germany 3
RTECS YQ2485000
TSCA Yes
HS Code 29322090
toxicityThe acute oral LD50 in rats was reported as 18.5 g/kg (Jenner, Hagan, Taylor, Cook & Fitzhugh, 1964). Fatty infiltration of liver parenchymal cells occurred in rats fed 13-115 mg y-undecalactone for 5-9 days (Shillinger, 1950).
MSDS Information
ProviderLanguage
gamma-Undecanolactone English
SigmaAldrich English
ACROS English
ALFA English
Undecan-4-olide Usage And Synthesis
DescriptionGAMMA-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.
References
  1. https://www.sigmaaldrich.com/catalog/product/aldrich/w309109?lang=en&region=US
  2. https://pubchem.ncbi.nlm.nih.gov/compound/Gamma-undecalactone#section=Top
  3. http://www.thegoodscentscompany.com/data/rw1000822.html
  4. An, J. U., Y. C. Joo, and D. K. Oh. "New biotransformation process for production of the fragrant compound γ-dodecalactone from 10-hydroxystearate by permeabilized Waltomyces lipofer cells. " Applied & Environmental Microbiology 79.8(2013): 2636-2641.
Chemical Propertiesgamma-Undecalactone has a strong, fruity odor suggestive of peach (particularly on dilution). It has a pungent and sweet flavor also similar to peach.
Chemical PropertiesGAMMA-UNDECALACTONE is clear colourless liquid
OccurrenceReported found in hydrolyzed soy protein, butter, peach, apricot and passion fruit. Also reported found in fresh apple, guava fruit, fresh blackberry, heated butter, heated beef fat, ghee, pork fat, yellow passion fruit juice, cooked scented rice, origanum (Spanish) (Coridothymus cap. (L.) Rchb.), mountain papaya, starfruit, plumcot and chicken fat.
Uses4-Undecanolide is used in the study of primary mutagenicity screening of food additives used in Japan.
UsesTraditionally, 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.
DefinitionChEBI: Xi-gamma-Undecalactone is a lactone.
PreparationBy the action of sulfuric acid on undecylenic acid; also prepared starting form castor oil; from octanol-1 plus methylacrylate with di-ter-butylperoxide; from heptylethylene oxide and sodiomalonic ester.
Aroma threshold valuesDetection: 60 ppb
Taste threshold valuesTaste characteristics at 30 ppm: fatty, coconut, creamy, vanilla, nutty, macadamia and peach.
General Descriptionγ-Undecalactone is a volatile flavor constituent found in low-fat ice cream.
Flammability and ExplosibilityNotclassified
Undecan-4-olide Preparation Products And Raw materials
Raw materialsSodium carbonate-->Methyl acrylate-->1-Octanol-->Undecenoic acid-->BUTTER
Preparation Productsall-trans-Retinol-->4-Ketoundecanoicacid
BETA-BUTYROLACTONE Alantolactone Undecan-4-olide 1-Nonanal GAMMA-UNDECALACTONE DEHYDROCOSTUSLACTONE tetradecanal oxime Gibberellin A4 GAMMA-UNDECALACTONE, NATURAL SPICULISPORIC ACID GIBBERELLIC ACID POTASSIUM SALT Gibberellin A7 Sclareolide PICROTOXININ gibberellin A1 gibberellin A4 methyl ester Isoalantolactone GIBBERELLIN A9 METHYL ESTER

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