Cinnamic Acid (HCID 444539)

概要

Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia. It has a role as a plant metabolite. It is a member of cinnamic acids and a member of styrenes. It is a conjugate acid of a cinnamate.

名称と識別子

優先名称: Cinnamic Acid
IUPAC: (E)-3-phenylprop-2-enoic acid
現地名: trans-けい皮酸
英語名: trans-Cinnamic acid
分子式: C9H8O2
分子量: 148.16

名称と別名

CINNAMIC ACID621-82-93-Phenylacrylic acidPhenylacrylic acidZimtsaeure(E)-3-phenylprop-2-enoic acid3-Phenylpropenoic acid3-phenylprop-2-enoic acidbeta-Phenylacrylic acidCinnamic acid, (E)-Cinnamylic acidBenzenepropenoic acid

名称をさらに表示

trans-けい皮酸(E)-3-フェニルアクリル酸trans-3-フェニルアクリル酸(E)-3-フェニルプロペン酸(E)-3-フェニル-2-プロペン酸(E)-ベンゼンアクリル酸けい皮酸(E)-ベンゼンプロペン酸(E)-けい皮酸TRANS-桂皮酸ケイヒ酸trans-けい皮酸 [MALDI-TOF/MS マトリックス用]TRANS‐けい皮酸けい皮酸, TRANS-3-フェニルプロペノン酸3-PHENYL-2-PROPENOIC ACIDFEMA 2288(2E)-3-phenylprop-2-enoic acid(E)-Cinnamic acid(e)-2-propenoicaci(E)-3-Phenylacrylic acidTRANS-3-PHENYLACRYLIC ACIDtrans-Cinnamicacid 140-10-3

Benzylideneacetic acidFEMA No. 2288CINNAMIC ACIDUMCinnamic acid, trans-Kyselina skoricoveAcidum cinnamylicumU14A832J8DNSC-9189

データベース識別子

CAS: 140-10-3、621-82-9
PubChem CID: 444539
DTXSID: DTXSID5022489
ChEMBL: CHEMBL27246
ChEBI: CHEBI:27386
UNII: U14A832J8D
EC Number: 205-398-1、210-708-3
Nikkaji: J2.024I、J2.087G

物性

構造計算による物性

XLogP: 2.1
極性表面積: 37.3 Å²
水素結合供与体数: 1
水素結合受容体数: 2
回転可能結合数: 2
重原子数: 11
形式電荷: 0
複雑度: 155

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Organic Acids

SpringerMaterials PropertiesAngular frequency

Fragrances · 2 件

Fragrance Ingredient (Cinnamic acid) -> IFRA transparency List

Fragrance Ingredient (trans-Cinnamic acid) -> IFRA transparency List

LogP2.13

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Flavoring AgentsEU Flavoring substances

物理化学的性質

融点: 133 °C · 133 °C (lit.)
沸点: 300 °C · 300 °C(lit.)
比重(密度): 1.248 · 1.248
蒸気圧: 1.3 hPa · 1.3 hPa (128 °C)
屈折率: 1.5049 · 1.5049 (estimate)
闪点: 230 °F · >230 °F
貯蔵温度: 2 · 2-8°C
溶解性: 0.4 g/l · 0.4g/l
酸解離定数(Pka): 4.44 · 4.44(at 25℃)
外見: 結晶性粉末
色: 白～ほぼ白
比重: 0.91 · 0.91
臭い (Odor): 微臭
PH: 3 · 3-4 (0.4g/l, H2O, 20℃)
においのタイプ: バルサミコ
由来生物: synthetic
水溶解度: 0.4 g/L · 0.4g/L(20℃)
Merck: 14 · 14,2299
BRN: 1905952 · 1905952
Henry's Law Constant: 2.8 · 2.8×1011 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
安定性: Light Sensitive
主な用途: フレーバーそして香料
化粧品成分の機能: 香料スキンコンディショニング
InChI: 1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
InChIKey: WBYWAXJHAXSJNI-VOTSOKGWSA-N
SMILES: OC(=O)\C=C\c1ccccc1
LogP: 2.13 · 2.130
CAS データベース: 140 · 140-10-3(CAS DataBase Reference)
NISTの化学物質情報: Cinnamic acid(140-10-3)
EPAの化学物質情報: (E)-Cinnamic acid (140-10-3)

化学的性質

化学的特性White to almost white crystalline powder. Insoluble in water, slightly soluble in hot water, easily soluble in benzene, acetone, ether, glacial acetic acid and other organic solvents.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 97.8% (1644 of 1681) of all reports.

Not Classified

Aggregated GHS information provided per 1681 reports by companies from 7 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 76.1% (284 of 373) of all reports.

Warning

H315 (15.5%): Causes skin irritation [Warning Skin corrosion/irritation]

危険有害性情報

Regulatory Information · 6 件

Chemical: 2-Propenoic acid, 3-phenyl-, (E)-

Chemical: 2-Propenoic acid, 3-phenyl-

Regulation (EC) No 1831/2003 (amended)

Status: Active Update: 06-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23816

2-Propenoic acid, 3-phenyl-, (E)-: Does not have an individual approval but may be used under an appropriate group standard

Cinnamic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 2 件

IMAP assessments - Cinnamic acid: Human health tier II assessment

Hazards Summary · 2 件

A mild skin irritant; Causes gastrointestinal changes in acute oral studies of rats; [RTECS] Safe when used as a flavoring agent in food; [JECFA] An eye irritant; [Alfa Aesar MSDS] See Hydrocinnamic acid.

A mild skin and strong eye irritant; [Alfa Aesar MSDS] See Hydrocinnamic acid.

Hazard Classes and Categories · 2 件

Skin Irrit. 2 (15.5%)

Not Classified

毒性情報

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk: 1
tsca: TSCA listed
rtecs: GD7850000
毒性: LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg
hs_code: 29163900
risk_code: 36/37/38
化審法: (3)-1719
hazard_code: Xi
safety_code: 26-36-37/39
Hazard Classifications: Eye Irrit. 2
ストレージクラス: 13 - Non Combustible Solids

化学と産業

薬理情報

Cellular LocationsMembrane

用途と製造

Uses · 2 件

Occurs in storax, balsam of Peru, oil of cinnamon, and coca leaves (trans isomer); Used as a fragrance and flavoring agent; [Merck Index]

The trans- isomer is found in storax, balsam of Peru, oil of cinnamon, and coca leaves; Used as a fragrance and flavoring agent; [Merck Index] Used in perfumery and as an anthelmintic; [Alfa Aesar MSDS]

Household ProductsInformation on 1 consumer products that contain Cinnamic acid in the following categories is provided:

Use Classification · 6 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 件

2-Propenoic acid, 3-phenyl-, (2E)-: ACTIVE

2-Propenoic acid, 3-phenyl-: ACTIVE

応用分野 · 5 件

解説ケイ皮酸シス形とトランス形が考えられるが，シス形はアロケイ皮酸(allocinnamic acid)といわれ，不安定で，普通，トランス形として存在する．天然には，ソゴウ香油中に遊離またはエステルの形で，またトルーバルサムやペルーバルサム中にベンジルエステルとして含まれる．無色の針状晶．融点133 ℃，沸点304 ℃．エタノール，エーテルに可溶．アロケイ皮酸は，コカの葉にあり，融点の異なる(32，42，58，68 ℃)四つの多形が知られている．おもにエステルの形で香料や化粧品に用いられる．[CAS 140-10-3] 森北出版「化学辞典（第2版）

用途食品用着香料、医薬品原料

使用trans-Cinnamic acid is used in flavors, synthetic indigo and pharmaceuticals. It is involved in the production of methyl, ethyl and benzyl esters, which is used in the perfume industry. It serves as a precursor to the sweetener aspartame through enzyme-catalyzed amination to phenylalanine. It is a self-inhibitor produced by fungal spores to prevent germination. In addition, it is used to establish phenolic compounds by liquid chromatography, ultraviolet and mass spectrometry. It is utilized as a potential agent, thereby preventing lung tumor cells from metastasizing. Further, it induces intracellular release of calcium ions from the vacuole to the cytoplasm in order to trigger phytotoxicity in cucumber.

一般的な説明trans-Cinnamic acid is an α,β-unsaturated aromatic acid that can be used as a flavoring agent. It is mainly used to prepare ester derivatives that are used in perfume industry. trans-Cinnamic acid is the key volatile components of cinnamon essential oil.

使用用途ケイ皮酸の使用用途は、除草剤、植物成長阻害剤、殺菌持続剤、防腐剤などです。また、ケイ皮酸のエステル誘導体は、香料や食品添加物、化粧品、農業用薬品の原料として使用されています。例えば、ケイ皮酸メチルとケイ皮酸エチルは、主にフレーバーとして食品添加物に使用されている物質です。医薬品としては、局部麻酔剤、殺菌剤や止血薬の製造や発赤剤などとして使用されています。さらに、その他の誘導体としては、メトキシケイヒ酸エチルヘキシルやジイソプロピルケイヒ酸メチルなどの物質は高い紫外線吸収能力があることから、褪色防止剤、紫外線吸収剤・散乱剤などの化粧品として利用されています。

調製方法

純化方法Crystallise the acid from *benzene, CCl4, hot water, water/EtOH (3:1), or 20% aqueous EtOH. Dry it at 60o in vacuo. It is steam volatile. [Beilstein 9 IV 2002.]

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補足説明 · 1 件

定義ChEBI: Cinnamic acid is a monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia. It has a role as a plant metabolite. It is a member of styrenes and a member of cinnamic acids. It is a conjugate acid of a cinnamate.

Cinnamic Acid

基本情報

概要