2-Phenylpropanal

HCID 7146CAS 93-53-8
Substructure searchFind similar structures

Basic information

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class of phenylacetaldehydes that is phenylacetaldehyde in which a hydrogen alpha to the aldehyde carbonyl group has been replaced by a methyl group.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 properties

XLogP
1.9
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
10

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 · 2 items

Soluble in most fixed oils; Slightly soluble in propylene glycol; Insoluble in glycerin

Soluble (in ethanol)

Physicochemical properties

Melting point
60 °C · 60°C
Boiling point
92 · 92-94 °C/12 mmHg (lit.)
Density
1.002 g/mL · 1.002 g/mL at 25 °C (lit.)
vapor pressure
40 Pa · 40Pa at 20℃
FEMA
2886 · 2886 | 2-PHENYLPROPIONALDEHYDE
refractive index
20 · n20/D 1.517(lit.)

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 4 items

Chemical: Benzeneacetaldehyde, .alpha.-methyl-

Regulation (EC) No 1831/2003 (amended)

Status: Active Update: 30-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/17307

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 · 1 item

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
hs_code
29122990
risk_code
36/37/38

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

UsesUsed as a flavoring agent; [FDA]
IFRA Fragrance Standards · 6 items

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 · 4 items

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 (%) · 6 items

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 · 4 items

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.

OccurrenceReported found in microbially fermented tea and some varieties of mushrooms.

Uses2-Phenylpropionaldehyde is a precursor in the synthesis of N,N,β-Trimethyl-phenethylamine Hydrochloride (T796625).

General Description2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor.

Preparation methods

PreparationBy alkaline condensation of acetophenone and ethyl chloroacetate; also by distillation of methylphenyl ethylene glycol in 91% yields (under atmospheric pressure).

Upstream & downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

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Linked notes

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