Basic information
- CAS
104-54-1- Standard SMILES
OC/C=C/c1ccccc1- InChIKey
OOCCDEMITAIZTP-QPJJXVBHSA-N- Molecular formula
- C9H10O
- Average molar mass
- 134.17 g/mol
- Monoisotopic mass
- 134.07316494
Overview
Cinnamyl alcohol is a primary alcohol comprising an allyl core with a hydroxy substituent at the 1-position and a phenyl substituent at the 3-position (geometry of the C=C bond unspecified). It has a role as a plant metabolite.
Names & identifiers
- Preferred name
- Cinnamyl Alcohol
- IUPAC
- (E)-3-phenylprop-2-en-1-ol
- English name
- 3-Phenyl-2-propen-1-ol
- Molecular formula
- C9H10O
- Molecular weight
- 134.18
Names & synonyms
cinnamyl alcohol104-54-1cinnamic alcohol3-PHENYL-2-PROPEN-1-OL(E)-3-phenylprop-2-en-1-ol(E)-cinnamyl alcoholStyryl carbinolStyrone3-Phenylallyl alcoholStyryl alcoholZimtalcohol(E)-3-Phenyl-2-propen-1-ol
Show more names
Cinnamyl Alcohol >2-Propen-1-ol, 3-phenyl-, (2E)-C11667500 trans-Cinnamyl-alcohol(E)-3-Phenylprop-2-en-1-ol (Cinnamyl alcohol)
2-Propen-1-ol, 3-phenyl-StyrylcarbinolFEMA No. 2294Alkohol skoricovyNSC-8775SS8YOP444FNSC-623440CHEBI:33227
Database identifiers
- CAS
104-54-1、4407-36-7- PubChem CID
- 5315892
- DTXSID
DTXSID301314144- ChEMBL
CHEMBL324794- ChEBI
CHEBI:17177- UNII
- SS8YOP444F
- EC Number
- 203-212-3、689-359-8
- Nikkaji
- J106.769I、J9.304A
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 101
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Other Aromatic Compounds
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetics ingredient -> Base; Flavor; Fragrance; Other (Specify)
Cosmetic ingredients (Cinnamyl Alcohol) -> CIR (Cosmetic Ingredient Review)
Masking
SpringerMaterials PropertiesOptical coefficient
Fragrances
Fragrance substance (Cinnamic alcohol) -> IFRA amendment 49
Fragrance Ingredient (Cinnamyl alcohol) -> IFRA transparency List
LogP
1.700
1.95
Odor
ODOR OF HYACINTH
PLEASANT, FLORAL ODOR
TasteBITTER TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 2033) of reports.
Warning
H302 (15.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2033 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Hazard information
Regulatory Information
Chemical: 2-Propen-1-ol, 3-phenyl-
Hazard Traits - Fragrance Allergen
Regulation (EC) No 1831/2003 (amended)
2-Propen-1-ol, 3-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propen-1-ol, 3-phenyl- 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: 25-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/12023
Cinnamyl alcohol: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2-Propen-1-ol, 3-phenyl-: Human health tier II assessment
Hazards Summary
Cinnamic alcohol was an allergen in 15 of 20 perfume-sensitive patients patch tested. [HSDB] An irritant; [MSDSonline] Positive patch tests reported in perfume industry and food handlers; One of the chemicals in the fragrance mix; [Kanerva, p. 1771] Included in list of established contact allergens in humans; [EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] Danger of skin sensitization; [MAK]
FDA Requirements121.1164
Chemistry & industry
Pharmacology
Metabolism/Metabolites
In general, esters containing an aromatic ring system are expected to be hydrolyzed in vivo. Cinnamyl alcohol is hydrolyzed to [DB14184].
ACIDIC & NEUTRAL URINARY METABOLITE OF CINNAMYL ALC WAS IDENTIFIED THROUGH A COMMON METABOLIC SCHEME.
Cinnamyl alcohol is a known human metabolite of beta-methylstyrene.
FDA Pharmacological Classification
SS8YOP444F
CINNAMYL ALCOHOL
Established Pharmacologic Class [EPC] - Standardized Chemical Allergen
Physiologic Effects [PE] - Increased Histamine Release
Physiologic Effects [PE] - Cell-mediated Immunity
Chemical Structure [CS] - Allergens
Absorption, Distribution and Excretion
Cinnamyl alcohol is 66% absorbed through the skin and shown to be rapidly absorbed from the gut.
Cinnamyl alcohol is metabolized and excreted primarily in the urine and, to a minor extent, in the feces. After oral or intraperitoneal administration to rats and mice, 76–77% of the dose of cinnamyl alcohol was recovered in the urine and feces within 24 h.
CINNAMYL ALC IS EXCRETED UNCHANGED IN NEUTRAL EXTRACT WHEN GIVEN TO RATS.
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
CIR ingredient: Cinnamyl Alcohol
Used as a fragrance, flavoring agent, deodorant, and chemical intermediate (chemical resistant coatings, photosensitive polymers, and lithographic plates); [HSDB]
AS DEODORANT IN 12.5% SOLN IN GLYCEROL
FRAGRANCE, EG, FOR COLOGNES, SOAPS, AND LOTIONS; FIXATIVE FOR PERFUME BLENDS; IN MFR OF CHEM RESISTANT COATINGS; FLAVORING AGENT FOR FOOD (EG, CANDY, GUM, BEVERAGES); CHEM INTERMEDIATE FOR CINNAMYL ESTERS USED IN PERFUMERY; IN MFG OF PHOTOSENSITIVE POLYMERS & LITHOGRAPHIC PLATES
U.S. Exports
Related reactions
13 records
Compound notes
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