2-Phenylpropanal
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Basic information
- CAS
93-53-8- Standard SMILES
CC(C=O)c1ccccc1- InChIKey
IQVAERDLDAZARL-UHFFFAOYSA-N- Molecular formula
- C9H10O
- Average molar mass
- 134.17 g/mol
- Monoisotopic mass
- 134.07316494
Overview
2-phenylpropanal is a member of the class of phenylacetaldehydes that is phenylacetaldehyde in which a hydrogen alpha to the aldehyde carbonyl group has been replaced by a methyl group. The major species at pH 7.3.
Names & identifiers
- Preferred name
- 2-Phenylpropanal
- IUPAC
- 2-phenylpropanal
- English name
- 2-PHENYLPROPIONALDEHYDE
- Molecular formula
- C9H10O
- Molecular weight
- 134.18
Names & synonyms
2-Phenylpropanal2-PhenylpropionaldehydeHydratropaldehyde93-53-8Hydratropic aldehydeHyacinthalCumene aldehydeHydratropa aldehydeHydrotropic aldehyde2-Phenyl-1-propanalalpha-Phenylpropionaldehydealpha-Formylethylbenzene
Show more names
2-PHENYLPROPANOLFEMA 2886NSC 5231cumenealdehyde2-PHENYLPRPANAL
Aldehyd hydratropovyalpha-Methylphenylacetaldehydealpha-Methylbenzeneacetaldehyde2-phenylpropanaldehydealpha-Methyl-alpha-toluic aldehydeFEMA No. 2886DTXSID00526298JKX55PKZQ
Database identifiers
- CAS
93-53-8- PubChem CID
- 7146
- DTXSID
DTXSID0052629- ChEMBL
CHEMBL3730701- ChEBI
CHEBI:149463- UNII
- 8JKX55PKZQ
- EC Number
- 202-255-5
- Nikkaji
- J35.593C
Properties
Computed structural propertiesFilling in
- XLogP
- 1.9
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 103
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aldehydes
FragrancesFragrance Ingredient (2-Phenylpropionaldehyde) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.998-1.006
Flavoring AgentsEU Flavoring substances
Solubility
Soluble in most fixed oils; Slightly soluble in propylene glycol; Insoluble in glycerin
Soluble (in ethanol)
Boiling Point
92.00 to 94.00 °C. @ 12.00 mm Hg
202-205 °C
Refractive Index1.515-1.520
Physical Description
Liquid; [Alfa Aesar MSDS]
Colourless to pale yellow liquid; Intense, green, floral aroma reminiscent of hyacinth
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1680 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzeneacetaldehyde, .alpha.-methyl-
Regulation (EC) No 1831/2003 (amended)
REACH registered substance: Hydratropaldehyde (EC: 202-255-5)
2-Phenylpropionaldehyde: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzeneacetaldehyde, .alpha.-methyl-: Environment tier I assessment
Hazards Summary
Decreased sperm counts in 14-day oral study of male rats at 75 and 250 mg/kg/day; [EPA - TSCATS] Causes coma in oral lethal-dose studies of rats; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- F
- 9-23
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- CY1460000
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
IFRA Fragrance Standards
2-Phenylpropionaldehyde
Benzeneacetaldehyde, α-methyl-; Hydratropaldehyde; α-Methylphenylacetaldehyde; α-Methyltolualdehyde; 2-Phenylpropanal; α-Phenylpropionaldehyde; (R)-2-Phenylpropionaldehyde; (S)-2-Phenylpropionaldehyde; Hydratropic aldehyde (commercial name)
IFRA_STD_075.pdf
49
IFRA 51st Amendment - Guidance for the use of IFRA Standards
Restriction: This material should be used only in the limited quantity as stated in the Standard
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationBenzeneacetaldehyde, .alpha.-methyl-: ACTIVE
Restriction Limits in the Finished Product (%)
0.029 [Products applied to the lips]
0.0087 [Products applied to the axillae]
0.096 [Products applied to the face/body using fingertips]
0.16 [Products related to fine fragrances]
0.041 [Products applied to the body using the hands (palms), primarily leave-on (Body lotion)]
0.041 [Products applied to the face using the hands (palms), primarily leave-on (Face moisturizer)]
Applications
Description2-phenylpropionaldehyde is also known as 2-phenylpropanal. It belongs to the family of phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 2- phenylpropionaldehyde is a naturally occurring compound in various foods including roasted nuts, cooked potatoes, cheese, wine, fruit, vegetables, coffee, tea, and cocoa. 2-phenylpropionaldehyde is used as a flavoring agent. Once absorbed, 2-phenylpropionaldehyde can be converted to phenyl-substituted carboxylic acids, which can be conjugated with glucuronic acid and excreted in the urine. 2-phenylpropionaldehyde can also undergo β- oxidation to benzoic acid or phenylacetic acid derivatives, which are conjugated with glycine or glutamine before being excreted in the urine.
Related reactions
47 records
Compound notes
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