3-Phenylprop-2-En-1-Ol
Basic information
- CAS
104-54-1- Standard SMILES
OCC=Cc1ccccc1- InChIKey
OOCCDEMITAIZTP-UHFFFAOYSA-N- Molecular formula
- C9H10O
- Average molar mass
- 134.17 g/mol
- Monoisotopic mass
- 134.07316494
Overview
3-phenyl-2-propen-1-ol has been reported in Rhodiola sachalinensis, Zanthoxylum ovalifolium, and other organisms with data available.
Names & identifiers
- Preferred name
- 3-Phenylprop-2-En-1-Ol
- IUPAC
- 3-phenylprop-2-en-1-ol
- English name
- Cinnamyl alcohol
- Molecular formula
- C9H10O
- Molecular weight
- 134.18
Names & synonyms
RefChem:10684943-Phenylprop-2-En-1-OlPhenylallyl alcohol1-Phenyl-1-propen-3-ol3-Phenyl-2-propenoltrans-cinnamic alcoholPhenyl-2-propen-1-olgamma-Phenylallyl alcoholstyrene-methanolPhenyl-2-propenol(Hydroxymethyl)styreneCinnamyl alcohol, 8CI
Show more names
CINNAMIC ALCOHOL3-PHENYL-2-PROPEN-1-OLTRANS-CINNAMYL ALCOHOLSterone(E)-3-phenyl-2-propen-1-olFEMA 22943-PHENYLALLYL ALCOHOL3-PhenylCinnamylalkohol
(3-phenyl)-allyl alcohol3-phenyl-prop-2-en-1-olSCHEMBL39220SCHEMBL97892SCHEMBL729778orb1222905orb1301286orb3025775
Database identifiers
- CAS
104-54-1- PubChem CID
- 308
- DTXSID
DTXSID9041491- ChEMBL
CHEMBL3183153
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
SpringerMaterials PropertiesAngular frequency
LogP1.95
Boiling Point250.00 to 258.00 °C. @ 760.00 mm Hg
Melting Point33 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 30 · 30-33 °C (lit.)
- Boiling point
- 250 °C · 250 °C (lit.)
- Density
- 1.044 g/mL · 1.044 g/mL at 25 °C (lit.)
- vapor density
- 4.6 · 4.6 (vs air)
- vapor pressure
- 0.01 mm · <0.01 mm Hg ( 25 °C)
- refractive index
- 1.5819 · 1.5819
- FEMA
- 2294 · 2294 | CINNAMYL ALCOHOL
- FLAVIS Number
- 2.017 · 02.017 | Cinnamyl alcohol
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-23
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- GE2200000
- ridadr
- 2811
- hs_code
- 29062990
- Toxicity
- LD50 (g/kg): 2.0 orally in rats; >5.0 dermally in rabbits (Letizia)
- risk_code
- 22-36/38-43-36
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- Xn
- safety_code
- 26-36/37-37/39-24-24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H302-H317-H411
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Skin Sens. 1
- Precautionary statements
- P261-P264-P273-P280-P301+P312-P302+P352
- Hazardous Substances Data
- 104-54-1(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
Use ClassificationFlavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
DescriptionAs an organic compound, Cinnamyl alcohol has a very distinct sweet, spicy, hyacinth odour that is found in resins, balsams and cinnamon leaves. It is used commonly in the fragrance industry due to its distinctive odour, which can be applied as a deodorant, fragrance and additive in cosmetic products and in the formulation of bath products, body and hand products, such as soaps, toothpaste, deodorants, etc. Besides, it also finds application as a food additive in chewing gum, bakery products, candy and soft drinks. Naturally, Cinnamyl alcohol is occurrent only in small amount, thus its industrial demand is usually fulfilled by chemical synthesis starting from the reduction of cinnamaldehyde. Cinnamyl alcohol has been found to have a sensitising effect on some particular people, thus it is also considered as a Standardized Chemical Allergen. The physiologic effect of cinnamyl alcohol is caused by the Increased Histamine Release and cell-mediated Immunity.
UsesCinnamyl alcohol is valuable in perfumery for its odor and fixative properties. It is a component of many flower compositions (lilac, hyacinth, and lily of the valley) and is a starting material for cinnamyl esters, several of which are valuable fragrance materials. In flavor compositions, the alcohol is used for cinnamon notes and for rounding off fruit aromas.
DescriptionOccupational cases of contact dermatitis were reported in the perfurne industry. Patch tests can also be positive in food handlers. Cinnamic alcohol is contained in the "fragrance mix".
OccurrenceOccurring as an ester or in the free state in hyacinth, Aristolochia clematis, Xanthorrhoea hastilis and in the essence of daffodil flowers. It is also reported found in guava fruit and peel, lemon peel oil, cassia leaf, Bourbon vanilla and cinnamon bark, leaf and root.
Related reactions
147 records
Compound notes
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