磷酸异丙酯(单双酯混合物) (HCID 14340)

概述

Dihydroferulic acid is a monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group. It has a role as an antioxidant, a mouse metabolite, a plant metabolite and a human xenobiotic metabolite. It is a member of guaiacols, a monocarboxylic acid and a phenylpropanoid. It is functionally related to a propionic acid. It is a conjugate acid of a dihydroferulate.

名称与标识

首选名称: Dihydroferulic Acid
IUPAC: 3-(4-hydroxy-3-methoxyphenyl)propanoic acid
中文名: 磷酸异丙酯(单双酯混合物)
英文名: 3-(4-Hydroxy-3-methoxyphenyl)propionic acid
分子式: C10H12O4
分子量: 196.2

名称与别名

1135-23-5dihydroferulic acid3-(4-Hydroxy-3-methoxyphenyl)propanoic acid3-(4-Hydroxy-3-methoxyphenyl)propionic acidDihydroconiferylic acidBenzenepropanoic acid, 4-hydroxy-3-methoxy-O01RNC700M3-(4-hydroxy-3-methoxy-phenyl)propanoic acidCHEBI:86612DTXSID90150427RefChem:133817DTXCID2072918

展开更多名称

二氢阿魏酸氢化阿魏酸3-(4-羟基甲基)丙酸3?(4?羟甲基) 丙酸磷酸异丙酯(单双酯混合物)3-甲氧基-4-羟基苯丙酸4-羟基-3-甲氧基苯基丙酸3-(4-羟基-3-甲氧苯基)丙酸3-(4-羟基-3-甲氧基苯基)丙酸氢化阿魏酸,10 MM DMSO 溶液Shorbic Acid3-METHOXY-4-HYDROXYHYDROCINNAMIC ACID3-(3-METHOXY-4-HYDROXYPHENYL)-PROPIONIC ACIDBETA-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACIDHYDROFERULIC ACID(RG)Ferulic Acid Impurity 1

214-489-5Hydroferulic acid3-(4-Hydroxymethyl)propionic acidMFCD00016558Dihydro Ferulic Acid4-Hydroxy-3-methoxy-benzenepropanoic acid3-METHOXYPHLORETIC ACID.beta.-(4-Hydroxy-3-methoxyphenyl)propionic acid

数据库标识

CAS: 1135-23-5
PubChem CID: 14340
DTXSID: DTXSID90150427
ChEMBL: CHEMBL387842
ChEBI: CHEBI:86612
UNII: O01RNC700M
EC Number: 214-489-5
Nikkaji: J203.383F

性质

结构计算性质

XLogP: 0.7
极性表面积: 66.8 Å²
氢键供体: 2
氢键受体: 4
可旋转键: 4
重原子: 14
形式电荷: 0
复杂度: 193

物理化学性质

熔点: 87 · 87-93 °C
沸点: 120 · 120-130 °C(Press: 0.5 Torr)
密度: 1.259 · 1.259±0.06 g/cm3(Predicted)
储存条件: 2 · Storage temp. 2-8°C
溶解度: Soluble in dimethyl sulfoxide and methanol.
形态: powder to crystal
酸度系数(pKa): 4.73 · 4.73±0.10(Predicted)
颜色: White to Light yellow
BRN: 2110370 · 2110370
InChI: InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
InChIKey: BOLQJTPHPSDZHR-UHFFFAOYSA-N
SMILES: C1(CCC(O)=O)=CC=C(O)C(OC)=C1
LogP: 0.81 · 0.810 (est)
CAS 数据库: 1135 · 1135-23-5(CAS DataBase Reference)

安全与法规

GHS分类

GHS Classification · 4 条

Warning

H302 (86.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危害信息

Hazard Classes and CategoriesAcute Tox. 4 (86.7%)

安全数据

wgk: 2
危险等级: IRRITANT
存储类别: 11 - Combustible Solids
安全说明: 26-36
海关编码: 29189900
危险品标志: Xn
危险性类别: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
危险类别码: 22-36/37/38

化学与工业

药理信息

Metabolism/MetabolitesDihydroferulic acid has known human metabolites that include 3-[3-Methoxy-4-(sulfooxy)phenyl]propanoic acid.

制备方法 · 1 条

生产方法以3-甲氧基-4-羟基苯基丙烯酸为原料合成磷酸异丙酯(单双酯混合物)的一般步骤如下：向搅拌的阿魏酸（25g，128.74mmol）在甲醇（200ml）中的悬浮液中加入Pd/C催化剂（3.75g）。将反应混合物置于1.2MPa氢气压力下，在50℃条件下氢化4小时。反应完成后，将混合物冷却至室温，过滤去除催化剂，并通过减压浓缩得到白色固体产物（25g，收率99%）。产物的结构通过1H NMR（400MHz，CDCl3）和ESI-MS进行确认：1H NMR δ 6.76（d, J = 7.8Hz, 1H），6.62（m, 2H），3.79（s, 3H），2.81（t, J = 7.7Hz, 2H），2.58（t, J = 7.7Hz, 2H）；ESI-MS m/z: 195.1 [M-H]。参考文献：[1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 1, p. 81 - 86[2] Tetrahedron Letters, 2010, vol. 51, # 44, p. 5753 - 5756[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4462 - 4466[4] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 429 - 439[5] Journal of the American Chemical Society, 2017, vol. 139, # 10, p. 3767 - 3773