基本情報
- CAS
501-98-4- 標準SMILES
O=C(O)/C=C/c1ccc(O)cc1- InChIKey
NGSWKAQJJWESNS-ZZXKWVIFSA-N- 分子式
- C9H8O3
- 平均分子量
- 164.16 g/mol
- 単同位体質量
- 164.04734412
概要
4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.
名称と識別子
- 優先名称
- P-Coumaric Acid
- IUPAC
- (E)-3-(4-hydroxyphenyl)prop-2-enoic acid
- 現地名
- trans-p-クマル酸
- 英語名
- p-Coumaric acid
- 分子式
- C9H8O3
- 分子量
- 164.16
名称と別名
p-coumaric acidtrans-p-Coumaric acidHydroxycinnamic acidPara-Coumaric acidNaringeninic acid(E)-p-Coumaric acidtrans-4-coumaric acidtrans-p-Hydroxycinnamic acidtrans-p-Coumarinic acid4'-hydroxycinnamic acid(E)-p-Hydroxycinnamic acid2-propenoic acid, 3-(4-hydroxyphenyl)-, (2E)-
名称をさらに表示
trans-p-クマル酸(E)-3-(4-ヒドロキシフェニル)-2-プロペン酸(E)-3-[4-ヒドロキシフェニル]アクリル酸p-ヒドロキシけい皮酸(E)-3-(4-ヒドロキシフェニル)プロペン酸trans-p-クマリン酸(E)-3-(4-ヒドロキシフェニル)アクリル酸4-ヒドロキシ-trans-けい皮酸(E)-p-クマル酸(2E)-3-(4-ヒドロキシフェニル)プロペン酸(E)-β-(4-ヒドロキシフェニル)アクリル酸4-ヒドロキシけい皮酸(E)-4-ヒドロキシけい皮酸p-trans-クマリン酸pヒドロキシケイヒ酸trans-4-ヒドロキシけい皮酸TRANS‐P‐クマル酸クマル酸, TRANS-P-(2E)-3-(4-ヒドロキシフェニル)プロパ-2-エン酸(E)-3-(4-hydroxyphenyl)acrylic acidp-CouMaricTRANS-4-HYDROXYCINNAMIC ACIDP-CUMARIC ACID(e)-p-coumaricacid
p-Hydroxyphenylacrylic acidCinnamic acid, p-hydroxy-3-(4-Hydroxyphenyl)-2-propenoic acid(E)-3-(4-Hydroxyphenyl)-2-propenoic acidbeta-(4-Hydroxyphenyl)acrylic acidCinnamic acid, p-hydroxy-, (E)-(2E)-3-(4-hydroxyphenyl)acrylic acidIBS9D1EU3J
データベース識別子
- CAS
501-98-4、7400-08-0- PubChem CID
- 637542
- DTXSID
DTXSID30901076- ChEMBL
CHEMBL66879- ChEBI
CHEBI:36090- UNII
- IBS9D1EU3J
- EC Number
- 231-000-0、610-511-6
- Nikkaji
- J6.196D、J8.929J
物性
構造計算による物性
- XLogP
- 1.5
- 極性表面積
- 57.5 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 2
- 重原子数
- 12
- 形式電荷
- 0
- 複雑度
- 178
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Skin conditioning
Personal care product
SpringerMaterials PropertiesChemical diffusion
LogP1.79
Melting Point211.5 °C
Physical DescriptionSolid
Collision Cross Section
127 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
131.1 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
131.3 Ų [M-H]-
物理化学的性質
- 融点
- 214 °C · 214 °C (dec.)(lit.)
- 沸点
- 231.61 °C · 231.61°C (rough estimate)
- 比重(密度)
- 1.1403 · 1.1403 (rough estimate)
- 屈折率
- 1.45 · 1.4500 (estimate)
- 貯蔵温度
- Keep in dark place,Sealed in dry,Room Temperature
- 溶解性
- 50 mg/mL · エタノール：可溶50mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 4.65 · 4.65±0.10(Predicted)
- 色
- オフホワイトからベージュまたは緑がかった色
- 臭い (Odor)
- 100 · 100.00?%で。バルサミコ
- 水溶解度
- 溶ける
- Merck
- 14 · 14,2560
- BRN
- 2207383 · 2207383
- Henry's Law Constant
- 7.2 · 7.2×105 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
- 安定性
- Light Sensitive
- 主な用途
- 食品および飲料
- InChI
- 1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3+
- InChIKey
- NGSWKAQJJWESNS-ZZXKWVIFSA-N
- SMILES
- OC(=O)\C=C\c1ccc(O)cc1
- LogP
- 1.46 · 1.460
- CAS データベース
- 501 · 501-98-4(CAS DataBase Reference)
- NISTの化学物質情報
- p-Hydroxycinnamic acid(501-98-4)
- EPAの化学物質情報
- 2 · 2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2E)- (501-98-4)
化学的性質
化学的特性Off-white to beige or greenish powder. Soluble in alcohol, ether and hot water, slightly soluble in benzene, insoluble in petroleum ether.
安全と法規制
GHS分類
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 75 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H301+H311 (63.6%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]
危険有害性情報
Regulatory Information
Status: Active Update: 28-08-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26756
4-Hydroxycinnamic acid, trans: Does not have an individual approval but may be used under an appropriate group standard
4-Hydroxycinnamic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Acute Tox. 3 (68.2%)
Skin Irrit. 2 (100%)
安全データ
- wgk
- 2
- rtecs
- GD9095000
- hs_code
- 29163990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Chemical substances or agents with contraceptive activity in males. Use for male contraceptive agents in general or for which there is no specific heading.
Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY.
Tissue LocationsFibroblasts
Cellular LocationsCytoplasm
用途と製造
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing Information2-Propenoic acid, 3-(4-hydroxyphenyl)-: ACTIVE
応用分野
用途有機合成原料。
調製方法
製造方法Synthesis of p-Coumaric acid: take o-acetylsalicyloyl chloride as raw material, in the presence of magnesium chloride, react with diethyl malonate in acetonitrile solvent, then add triethylamine, and react at 0°C for 1 h to obtain ( 2-acetoxybenzoyl) diethyl malonate product, then heated to 50°C in potassium hydroxide/methanol solution, reacted for 3h, and cyclized to obtain p-Coumaric acid.
純化方法Crystallise p-coumaric acid from H2O (charcoal). It forms needles from concentrated aqueous solutions as the anhydrous acid, but from hot dilute solutions the monohydrate acid separates on slow cooling. The acid (33g) has been crystallised from 2.5L of H2O (1.5g charcoal) yielding 28.4g of recrystallised acid, m 207o. It is insoluble in *C6H6 or pet ether. The UV in 95% EtOH has max 223 and 286nm ( 14,450 and 19000 M-1cm-1). [UV Wheeler & Covarrubias J Org Chem 28 2015 1963, Corti Helv Chim Acta 32 681 1949, Beilstein 10 IV 1005.]
上流・下流製品情報
上流原料
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補足説明
定義ChEBI: p-coumaric acid is the trans-isomer of 4-coumaric acid. 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.
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