Undecan-4-olide
- Iupac Name：5-heptyloxolan-2-one
- CAS No.: 104-67-6
- Molecular Weight：184.279
- Modify Date.: 2022-11-29 09:46
- Introduction: 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.
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1. Names and Identifiers
- 1.1 Name
- Undecan-4-olide
- 1.2 Synonyms
1,4-UNDECANOLIDE 2(3H)-Furanone, 5-heptyldihydro- 4-Hydroxyundecanoic acid lactone 4-Hydroxyundecanoic acid, Γ-lactone 4-Undecanolide 5-heptyl-2-tetrahydrofuranone 5-Heptyldihydro-2(3H)-furanone 5-Heptyldihydrofuran-2(3H)-one 5-heptyl-dihydro-furan-2-one Aldehyde C14 ALDEHYDE C-14 Dihydro-5-heptyl-2(3H)-furanone EINECS 203-225-4 FEMA 3091 GAMMA-HEPTYL-GAMMA-BUTYROLACTONE GAMMA-UNDECALACTONE GAMMA-UNDECANOLACTONE G-N-HEPTYLBUTYROLACTONE G-UNDECALACTONE MFCD00005405 Peach PEACH ALDEHYDE Peach lactone Persicol rersicol undecan-4 Undecanoic acid, 4-hydroxy-, Γ-lactone Undecanoic Γ-lactone UNII:QB1T0AG2YL Γ-Heptylbutyrolactone Γ-Heptyl-Γ-butyrolactone Γ-Undecalactone Γ-Undecanolactone Γ-Undecanolide
- 1.3 CAS No.
- 104-67-6
- 1.4 CID
- 7714
- 1.5 EINECS(EC#)
- 203-225-4
- 1.6 Molecular Formula
- C11H20O2 (isomer)
- 1.7 Inchi
- InChI=1S/C11H20O2/c1-2-3-4-5-6-7-10-8-9-11(12)13-10/h10H,2-9H2,1H3
- 1.8 InChkey
- PHXATPHONSXBIL-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CCCCCCCC1CCC(=O)O1
- 1.10 Isomers Smiles
- CCCCCCCC1CCC(=O)O1
2. Properties
- 2.1 Density
- 0.9425
- 2.1 Melting point
- 164～166℃
- 2.1 Boiling point
- 164-166℃ (13 torr)
- 2.1 Refractive index
- 1.449
- 2.1 Flash Point
- 137℃
- 2.1 Precise Quality
- 184.14600
- 2.1 PSA
- 26.30000
- 2.1 logP
- 3.05250
- 2.1 Appearance
- Clear colorless Liquid
- 2.2 Storage
- Ambient temperatures.
- 2.3 Chemical Properties
- GAMMA-UNDECALACTONE is clear colourless liquid
- 2.4 Color/Form
- Clear colorless
- 2.5 Water Solubility
- soluble in alcohol, most fixed oils and propylene glycol; insoluble in glycerol and in water
- 2.6 StorageTemp
- Sealed in dry,Room Temperature
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- Undecylenic acid obtained by heating cracking of castor seed oil is formed by heating and cyclization with the participation of sulfuric acid (80~90℃, 6~8h).
- 3.2 Usage
- 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. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi;
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R36/37/38
- 4.1 Safety Statements
- 26-36/37/39
- 4.1 Hazard Declaration
- H315-H319-H335-H412
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P261-P273-P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- YQ2485000
- 4.1 Toxicity
- The acute oral LD 50 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).
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | H412 Harmful to aquatic life with long lasting effects |
| Precautionary statement(s) | |
| Prevention | P273 Avoid release to the environment. |
| Response | none |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
104-67-6Total: 30 Synthesis Route
9. Other Information
- 9.0 BRN
- 81943
- 9.1 Chemical Properties
- clear colourless liquid
- 9.2 Production
- 1,000,000 - 10,000,000 lb
- 9.3 Manufacturing Info
- All other chemical product and preparation manufacturing|2(3H)-Furanone, 5-heptyldihydro-: ACTIVE
- 9.4 Use Classification
- EPA Safer Chemical Functional Use Classes -> Fragrances|Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern|Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]|Cosmetics -> Masking; Solvent
- 9.5 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.
- 9.6 References
-
- https://www.sigmaaldrich.com/catalog/product/aldrich/w309109?lang=en®ion=US
- https://pubchem.ncbi.nlm.nih.gov/compound/Gamma-undecalactone#section=Top
- http://www.thegoodscentscompany.com/data/rw1000822.html
- 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.
- 9.7 Chemical Properties
- GAMMA-UNDECALACTONE is clear colourless liquid
- 9.8 Chemical Properties
- gamma-Undecalactone has a strong, fruity odor suggestive of peach (particularly on dilution). It has a pungent and sweet flavor also similar to peach.
- 9.9 Occurrence
- Reported 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.
- 9.10 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.
- 9.11 Uses
- 4-Undecanolide is used in the study of primary mutagenicity screening of food additives used in Japan.
- 9.12 Preparation
- By 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.
- 9.13 Aroma threshold values
- Detection: 60 ppb
- 9.14 Taste threshold values
- Taste characteristics at 30 ppm: fatty, coconut, creamy, vanilla, nutty, macadamia and peach.
- 9.15 General Description
-
γ-Undecalactone is a volatile flavor constituent found in low-fat ice cream.
10. Computational chemical data
- Molecular Weight: 184.279g/mol
- Molecular Formula: C11H20O2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 184.146329876
- Monoisotopic Mass: 184.146329876
- Complexity: 154
- Rotatable Bond Count: 6
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 26.3
- Heavy Atom Count: 13
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 1
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADceBwMAAAAAAAAAAAAAAAAAAAASAAAAAAAAAAAAAAAAAAAAAAGgAAAAAACBSggAICCAAABAAIAACQCAAAAAAAAAAAAAEAAAAAABIAAAACAAAEAAAAAAGKyKCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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