Basic information
- CAS
112-37-8- Standard SMILES
CCCCCCCCCCC(=O)O- InChIKey
ZDPHROOEEOARMN-UHFFFAOYSA-N- Molecular formula
- C11H22O2
- Average molar mass
- 186.29 g/mol
- Monoisotopic mass
- 186.16197994
Overview
Undecanoic acid is a white crystalline solid. Insoluble in water. Specific gravity 0.85. Hence floats on water.
Names & identifiers
- Preferred name
- Undecanoic Acid
- IUPAC
- undecanoic acid
- English name
- Hendecanoic acid
- Molecular formula
- C11H22O2
- Molecular weight
- 186.29
Names & synonyms
UNDECANOIC ACID112-37-8Hendecanoic acidUndecylic acidn-Undecoic acidn-Undecanoic acidn-Undecylic acidUndecoic acid1-Decanecarboxylic acidDTXSID8021690NSC-7885138ON3IIQG
Show more names
FEMA 3245Hendecylic acidUNDECYCLIC ACIDCARBOXYLIC ACID C1111:0acid c-11AKOS 212-94Undecansαure
CHEBI:32368DTXCID001690RefChem:193083203-964-2undecanoateFEMA No. 3245Undecanoate [USAN]MFCD00002730
Database identifiers
- CAS
112-37-8- PubChem CID
- 8180
- DTXSID
DTXSID8021690- ChEMBL
CHEMBL108030- ChEBI
CHEBI:32368- UNII
- 138ON3IIQG
- EC Number
- 203-964-2
- Nikkaji
- J1.993C
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 9
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 121
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Organic Acids
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]
Cosmetics
Cosmetic ingredients (Undecanoic Acid) -> CIR (Cosmetic Ingredient Review)
Antiseborrhoeic; Cleansing; Emulsifying
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Undecanoic acid) -> IFRA transparency List
LogP
4.42
4.42
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
0.891 (USCG, 1999) - Less dense than water; will float
0.9948 (20 °C/20 °C)
Flavoring AgentsEU Flavoring substances
Solubility
0.0522 mg/mL
Insoluble in water; very soluble in alcohol, chloroform, acetone
(in ethanol)
Flash Pointgreater than 230 °F (USCG, 1999)
Boiling Point
442.2 °F at 160 mmHg (USCG, 1999)
284 °C
Physicochemical properties
- Melting point
- 28 · 28-31 °C(lit.)
- Boiling point
- 228 °C160 · 228 °C160 mm Hg(lit.)
- Density
- 0.89 g/cm3 · 0.89 g/cm3 (20℃)
- refractive index
- 1.4202 · 1.4202
- FEMA
- 3245 · 3245 | UNDECANOIC ACID
- FLAVIS Number
- 8.042 · 08.042 | Undecanoic acid
- Flash point
- 230 °F · >230 °F
- storage temp.
- room temp
- solubility
- 0.05 g/l · 0.05g/l insoluble
- form
- Low Melting Solid
- pka
- 4.79 · 4.79±0.10(Predicted)
- Specific Gravity
- 0.9948 · 0.9948
- color
- White to pale yellow
- Odor
- 100 % · at 100.00 %. waxy creamy cheese fatty coconut
- Odor Type
- waxy
- biological source
- synthetic
- explosive limit
- 0.6 % · 0.6%(V)
- Water Solubility
- insoluble
- Thermal Conductivity
- 0.165 W/ · 0.165 W/(m·K) at 25 ℃
- JECFA Number
- 108 · 108
- BRN
- 1759287 · 1759287
- Henry's Law Constant
- 7.7 · 7.7×100 mol/(m3Pa) at 25℃, Yaws (2003)
- Cosmetics Ingredients Functions
- SURFACTANT - EMULSIFYINGANTI-SEBUMFRAGRANCESURFACTANT - CLEANSINGCLEANSING
- InChI
- 1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
- InChIKey
- ZDPHROOEEOARMN-UHFFFAOYSA-N
- SMILES
- CCCCCCCCCCC(O)=O
- LogP
- 4.5 · 4.50
- CAS DataBase Reference
- 112 · 112-37-8(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- UNDECANOIC ACID
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 138 ON3IIQG · 138ON3IIQG
- NIST Chemistry Reference
- Undecanoic acid(112-37-8)
- EPA Substance Registry System
- Undecanoic acid (112-37-8)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 1 · 1
- RTECS
- 2275000 · YQ2275000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29159080 · 29159080
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 1.2% (2 of 167) of reports.
Warning
H315 (98.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 167 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Undecanoic acid
Undecanoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Undecanoic acid 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: 16-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/16828
Undecanoic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Fire HazardsSpecial Hazards of Combustion Products: Dust explosion is possible. (USCG, 1999)
Health HazardsMay be harmful by inhalation, ingestion or skin absorption. Material is irritating to mucous membrane and upper respiratory tract. Causes eye and skin irritation. (USCG, 1999)
Hazards Summary
A mild skin irritant; Causes convulsions in intravenous lethal-dose studies of mice; [RTECS] Causes severe skin irritation and serious eye injury; Brief contact can causes second- and third-degree skin burns; Vapors, dust, or mist causes severe eye and throat irritation and may cause injury to the eye and lung; [CHRIS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Sigma-Aldrich MSDS]
Reactive GroupAcids, Carboxylic
Reactivity Profile
A weak carboxylic acid. Neutralizes bases with the evolution of substantial amounts of heat to produce water plus a salt. Reacts with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Can generate flammable and/or toxic gases and heat by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts in with aqueous solutions of nitrites and thiosulfates (to give H2S and SO3) and dithionites (to give SO2) and heat. Reaction with solutions of carbonates and bicarbonates generate a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions. May serve as a catalyst.
Air and Water ReactionsDust explosion is possible. (USCG, 1999). Insoluble in water.
Hazard Classes and CategoriesSkin Irrit. 2 (98.8%)
Safety & protection
Fire FightingFire Extinguishing Agents Not to Be Used: Water may not be effective.
First AidINHALATION: Call for medical aid. Remove the victim to fresh air. If not breathing give artificial respiration. If breathing is difficult give oxygen.
Nonfire Spill ResponseNeutralizing Agents for Acids and Caustics: Sodium bicarbonate solution (USCG, 1999)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Toxicity Summary
The CIR Expert Panel concluded that the following ingredients are safe in the present practices of use andconcentration described in the safety assessment when formulated to be non-irritating and non-sensitizing, which may be basedon a QRA...Undecanoic Acid...
Safe for use in cosmetics, with qualifications
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- YQ2275000
- hs_code
- 29159080
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
Uses
CIR ingredient: Undecanoic Acid
Used as flavoring agent or adjuvant; [FDA]
U.S. Production2023: 50,000 - <250,000 lb
Consumer UsesSoil amendments (fertilizers)
Industry UsesSoil amendments (fertilizers)
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Cosmetics -> Antiseborrhoeic; Cleansing; Emulsifying
General Manufacturing Information
Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing
Undecanoic acid: ACTIVE
Applications
DescriptionHendecanoic acid (also known as undecanoic acid, undecylenic acid and undecylic acid) is a naturally occurring carboxylic acid. Its chemical formula is CH3(CH2)9COOH. It may participate in the control of triacylglycerol synthesis, and is found in breast milk and infant formula. It is known as an antifungal agent, used for the treatment of some types of fungal infections including ringworm and athlete’s foot. One of its mechanism of action is through inhibition of the morphogenesis of Candida albicans. It may also interfere with the fatty acid biosynthesis process of fungi. It is manufactured by the vacuum distillation of castor bean oil through the pyrolysis of ricinoleic acid. However, it has been generally replaced by new generation of anti-fungal medicine.
DescriptionUndecanoic acid is a saturated fatty acid containing eleven carbons (C11:0). It is cytotoxic to certain filamentous fungi and is used to study fungal mechanisms of resistance. Undecanoic acid is also used to acylate larger molecules.
OccurrenceOccurs naturally in butter and in the oil of Artemisisa frigida Willd.; also reported found in the oils of Chamaecyparis pisifera Engl., wild thyme, Thymus marschollianus and coconut. Also reported found in apple, banana, sour cherry, lemon and mandarin peel oil, grapefruit juice, guava, grapes, papaya, many cheeses, milk powder, chicken and beef fat, cooked mutton, cured pork, beer, cognac, rum, whiskies, white wine, tea, coconut milk, beans, licorice, mango, mushrooms, rice, sake, wort, loquat, scallop and maté.
UsesUndecanoic acid was used in the formation of cycloamylose crystals.
UsesIntermediates of Liquid Crystals
UsesUndecanoic Acid is a saturated fatty acid. It may be used to activate orphan G protein-coupled receptor GPR40.
General DescriptionWhite crystalline solid. Insoluble in water. Specific gravity 0.85. Hence floats on water.
Preparation methods
PreparationHendecanoic acid can be produced by reduction of Undecylenic acid, which is generally obtained from Castor oil.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A straight-chain, eleven-carbon saturated medium-chain fatty acid found in body fluids; the most fungitoxic of the C7:0 - C18:0 fatty acid series.
Related reactions
17 records
Compound notes
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