2-Phenylpropanal (HCID 7146)

概要

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class of phenylacetaldehydes that is phenylacetaldehyde in which a hydrogen alpha to the aldehyde carbonyl group has been replaced by a methyl group.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

名称と識別子

優先名称: 2-Phenylpropanal
IUPAC: 2-phenylpropanal
現地名: 2-フェニルプロピオンアルデヒド
英語名: 2-PHENYLPROPIONALDEHYDE
分子式: C9H10O
分子量: 134.18

名称と別名

2-Phenylpropanal2-PhenylpropionaldehydeHydratropaldehyde93-53-8Hydratropic aldehydeHyacinthalCumene aldehydeHydratropa aldehydeHydrotropic aldehyde2-Phenyl-1-propanalalpha-Phenylpropionaldehydealpha-Formylethylbenzene

名称をさらに表示

2-フェニルプロピオンアルデヒドヒドラトロパルデヒドヒアシンタールクメンアルデヒド2-フェニルプロパナールヒドラトロピックアルデヒドヒドロアトロパアルデヒドα-メチル-α-フェニルアセトアルデヒドヒドラトロパアルデヒド2-(フェニル)-1-プロパノンα-メチルベンゼンアセトアルデヒドヒドラトロプアルデヒドDL‐2‐フェニルプロピオンアルデヒド2-フェニルプロピオンアルデヒド, 98%2-PHENYLPROPANOLFEMA 2886NSC 5231cumenealdehyde2-PHENYLPRPANAL

Aldehyd hydratropovyalpha-Methylphenylacetaldehydealpha-Methylbenzeneacetaldehyde2-phenylpropanaldehydealpha-Methyl-alpha-toluic aldehydeFEMA No. 2886DTXSID00526298JKX55PKZQ

データベース識別子

CAS: 93-53-8
PubChem CID: 7146
DTXSID: DTXSID0052629
ChEMBL: CHEMBL3730701
ChEBI: CHEBI:149463
UNII: 8JKX55PKZQ
EC Number: 202-255-5
Nikkaji: J35.593C

物性

構造計算による物性

XLogP: 1.9
極性表面積: 17.1 Å²
水素結合供与体数: 0
水素結合受容体数: 1
回転可能結合数: 2
重原子数: 10
形式電荷: 0
複雑度: 103

実験および物理化学的性質

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 件

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

Soluble (in ethanol)

物理化学的性質

融点: 60 °C · 60°C
沸点: 92 · 92-94 °C/12 mmHg (lit.)
比重(密度): 1.002 g/mL · 1.002 g/mL at 25 °C (lit.)
蒸気圧: 40 Pa · 40Pa at 20℃
FEMA: 2886 · 2886 | 2-PHENYLPROPIONALDEHYDE
屈折率: 20 · n20/D 1.517(lit.)
闪点: 169 °F · 169 °F
貯蔵温度: 2 · 2-8°C
溶解性: ほとんどの固定油、プロピレングリコールに可溶。グリセリンに不溶。
外見: 液体
色: 無色透明
臭い (Odor): 10 %。新鮮な鋭い緑のヒヤシンスの葉、ライラック · ジプロピレングリコール中10.00%。新鮮な鋭い緑のヒヤシンスの葉、ライラック
においのタイプ: 緑
由来生物: synthetic
水溶解度: 10 μg/L · 10μg/L
JECFA Number: 1467 · 1467
BRN: 4291321 · 4291321
主な用途: 洗浄剤化粧品食品および飲料パーソナルケア
化粧品成分の機能: 香料
InChI: 1S/C9H10O/c1-8(7-10)9-5-3-2-4-6-9/h2-8H,1H3
InChIKey: IQVAERDLDAZARL-UHFFFAOYSA-N
SMILES: [H]C(=O)C(C)c1ccccc1
LogP: 1.96 · 1.96
CAS データベース: 93 · 93-53-8(CAS DataBase Reference)
EPAの化学物質情報: Benzeneacetaldehyde, .alpha.-methyl- (93-53-8)

化学的性質 · 1 件

化学的特性2-PHENYLPROPIONALDEHYDE identified in dried mushroom, is a colorless liquid with a green hyacinth odor. Hydratropaldehyde can be hydrogenated to hydratropic alcohol, which is also used to a limited extent by reaction of p-ethylbenzyl chloride and isobutyric aldehyde in the presence of catalysts. The product is used in perfumes for, for example, household products.

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 4 件

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 件

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%)

安全データ

F: 9-23
wgk: 3
tsca: TSCA listed
rtecs: CY1460000
hs_code: 29122990
risk_code: 36/37/38
化審法: (3)-2656, (3)-2913
消防法: 危-4-3-III
hazard_code: Xi
safety_code: 26-36/37/39
ストレージクラス: 10 - Combustible liquids

化学と産業

薬理情報

Cellular LocationsCytoplasm

用途と製造

UsesUsed as a flavoring agent; [FDA]

IFRA Fragrance Standards · 6 件

2-Phenylpropionaldehyde

Benzeneacetaldehyde, Î±-methyl-; Hydratropaldehyde; Î±-Methylphenylacetaldehyde; Î±-Methyltolualdehyde; 2-Phenylpropanal; Î±-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 件

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 件

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)]

応用分野 · 3 件

天然物の起源Reported found in microbially fermented tea and some varieties of mushrooms.

使用2-Phenylpropionaldehyde is a precursor in the synthesis of N,N,β-Trimethyl-phenethylamine Hydrochloride (T796625).

一般的な説明2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor.

調製方法 · 3 件

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

The most important synthetic route to 2-phenylpropionaldehyde is the rhodiumcatalyzed hydroformylation of styrene. The catalyst [HCo(CO)4] is unsuitable in this process because it favors the hydrogenation of styrene. The use of chiral rhodium complexes leads to the formation of optically active aldehydes when prochiral olefins, such as styrene, are used. Asymmetric hydroformylation, however, has so far found only small industrial application because of insufficient purity of the enantiomers. Other synthetic methods are the gas-phase oxidation of a-methylstyrene on Cu, Bi–Mo– P–SiO2, or Pd salt catalysts, the rearrangement of epoxidized a-methylstyrene, and the dehydrogenation of 2-phenyl-1-propanol on Ag catalysts at reaction temperatures of ca. 600 ℃.

純化方法It may contain up to 15% of acetophenone. Purify it via the bisulfite addition compound [Lodge & Heathcock J Am Chem Soc 109 3353 1987] and see Chapter 2 for preparation and decomposition of bisulfite adducts. [Beilstein 7 IV 695.]