Basic information
- CAS
104-67-6- Standard SMILES
CCCCCCCC1CCC(=O)O1- InChIKey
PHXATPHONSXBIL-UHFFFAOYSA-N- Molecular formula
- C11H20O2
- Average molar mass
- 184.27 g/mol
- Monoisotopic mass
- 184.14632988
Overview
Xi-gamma-Undecalactone is a lactone.
Names & identifiers
- Preferred name
- Gamma-undecalactone
- IUPAC
- 5-heptyloxolan-2-one
- English name
- Undecan-4-olide
- Molecular formula
- C11H20O2
- Molecular weight
- 184.28
Names & synonyms
Gamma-undecalactone104-67-6Undecan-4-olide5-heptyloxolan-2-one2(3H)-Furanone, 5-heptyldihydro-PersicolPeach aldehydePeach lactone5-Heptyldihydro-2(3H)-furanone1,4-Undecanolidegamma-UndecanolactoneAldehyde C-14 peach
Show more names
γ-UndecalactoneALDEHYDE C-14δ-Undecalactoneγ-Unsecalactoneγ-UndecalactonePeach
1,4-Hendecanolide4-Hydroxyundecanoic acid lactonegamma-Undecanolide.gamma.-UndecalactoneFEMA No. 3091gamma-Undekalaktongamma-Heptyl-gamma-butyrolactoneQB1T0AG2YL
Database identifiers
- CAS
104-67-6- PubChem CID
- 7714
- DTXSID
DTXSID4034287- ChEMBL
CHEMBL195827- ChEBI
CHEBI:89362- UNII
- QB1T0AG2YL
- EC Number
- 203-225-4
- Nikkaji
- J1.182G
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 6
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 154
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Lactones
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Lactones [FA0704]
CosmeticsMasking; Solvent
FragrancesFragrance Ingredient (gamma-Undecalactone) -> IFRA transparency List
Food Additives
FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Food
Density0.942-0.945
Flavoring AgentsEU Flavoring substances
Solubility
soluble in alcohol, most fixed oils and propylene glycol; insoluble in glycerol and in water
1 ml in 5 ml 60% alcohol (in ethanol)
Boiling Point297 °C
Refractive Index1.448-1.453
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 69.7% (1536 of 2205) of all reports.
H411 (10.3%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2205 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Chemical: 2(3H)-Furanone, 5-heptyldihydro-
Regulation (EC) No 1831/2003 (amended)
2(3H)-Furanone, 5-heptyldihydro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2(3H)-Furanone, 5-heptyldihydro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 12-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14215
1,4-Undecanolide: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
A moderate to severe skin irritant; Causes somnolence in oral lethal-dose studies of rats; [RTECS] No significant adverse effects observed in a 90-day or 2-year feeding studies of rats; Formulations contain 0.049% of this active ingredient and are of low acute toxicity; Limited supplementary studies from open literature for the pure substance also demonstrate low acute oral toxicity and at 2% in petroleum no irritation or sensitization to human skin; [Reference #1] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS] See Butyrolactone and gamma-Nonalactone.
Hazard Classes and Categories
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Uses & manufacturing
Uses
Used as repellent for cats and dogs, as insecticide/repellant for house flies, cockroaches, ants, biting flies, and mosquitoes, and as a mosquito larvicide for residential and large scale public health applications; [Reference #1] Used as flavoring agent or adjuvant; [FDA]
U.S. Production2023: 10,000,000 - <25,000,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesFragrance
Household ProductsInformation on 295 consumer products that contain 2(3H)-Furanone, 5-heptyldihydro- in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Cosmetics -> Masking; Solvent
General Manufacturing Information
Food, beverage, and tobacco product manufacturing
2(3H)-Furanone, 5-heptyldihydro-: ACTIVE
Applications
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.
Related reactions
14 records
Compound notes
Loading…