3-ヒドロキシプロピオン酸

3-Hydroxypropionic acid

HCID 68152CAS 503-66-2

基本情報

標準SMILES
O=C(O)CCO
InChIKey
ALRHLSYJTWAHJZ-UHFFFAOYSA-N
分子式
C3H6O3
平均分子量
90.08 g/mol
単同位体質量
90.03169405

概要

3-hydroxypropionic acid is a 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group. It has a role as an Escherichia coli metabolite and a human metabolite. It is an omega-hydroxy-short-chain fatty acid and a 3-hydroxy monocarboxylic acid. It is functionally related to a propionic acid. It is a conjugate acid of a 3-hydroxypropionate.

名称と識別子

優先名称
3-Hydroxypropionic acid
IUPAC
3-hydroxypropanoic acid
現地名
3-ヒドロキシプロピオン酸
英語名
3-Hydroxypropionic acid
分子式
C3H6O3
分子量
90.08

名称と別名

3-Hydroxypropionic acid503-66-23-Hydroxypropanoic acidHydracrylic acidbeta-Hydroxypropionic acidhydroxypropionic acidEthylene lactic acidbeta-Lactic acid3-HydroxypropanoateC4ZF6XLD2Xbeta-hydroxypropionateCHEBI:33404
名称をさらに表示
3-ヒドロキシプロピオン酸 (約30%水溶液, 約3.6mol/L)エチレン乳酸β-乳酸ヒドロアクリル酸β-オキシプロピオン酸3-ヒドロキシプロパン酸β-ヒドロキシプロピオン酸3-ヒドロキシプロパン酸 (30% SOLUTION IN WATER)3-ヒドロキシプロピオン酸, APPROX 30% IN WATER3-ヒドロキシプロピオン酸, 30% IN WATER3-ヒドロキシプロパン酸, 30% AQUEOUS SOLUTION3-ヒドロキシプロピオン酸3-ヒドロキシプロピオン酸溶液beta-lacticacid.beta.-Lacticacid2-deoxy-glycericaciRARECHEM AL BO 01932-deoxy-Glycericacid
DTXSID50198305RefChem:94392DTXCID40120796207-974-8Propanoic acid, 3-hydroxy-3-HYDROXY-PROPANOIC ACIDEthylenelacticacidGlyceric acid, 2-deoxy-

データベース識別子

CAS
503-66-2
PubChem CID
68152
DTXSID
DTXSID50198305
ChEMBL
CHEMBL1205969
ChEBI
CHEBI:33404
UNII
C4ZF6XLD2X
EC Number
207-974-8
Nikkaji
J6.213H

物性

構造計算による物性

XLogP
-1
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
6

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesDielectric constant
Melting Point< 25 °C
Physical DescriptionSolid

物理化学的性質

融点
16.8 °C · 16.8°C (estimate)
沸点
212 °C · 212°C (rough estimate)
比重(密度)
1.066 g/mL · 1.066 g/mL at 25 °C
屈折率
1.4489 · 1.4489
闪点
110 ° · >110°
貯蔵温度
2 · 2-8°C

化学的性質

化学性质アクリル酸の前駆体

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.

Danger

H302 (88.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+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 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (88.9%)

毒性情報

Health Effects · 1 件

Chronically high levels of hydroxypropionic acid are associated with at least 5 inborn errors of metabolism including: Biotinidase deficiency, Malonic Aciduria, Methylmalonate Semialdehyde Dehydrogenase Deficiency, Methylmalonic Aciduria, Methylmalonic, Aciduria Due to Cobalamin-Related Disorders and Propionic acidemia.

Toxicity Summary · 1 件

3-hydroxypropionic acid (3HP) toxicity is mediated by 3-hydroxypropionic aldehyde (reuterin). 3HP toxicity is also proposed to be related to inhibition of the chorismate and threonine super-pathways. Generally, the toxicity mechanism of 3HP is not understood at the molecular level. (A15450)

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

安全データ

wgk
WGK 1
hs_code
29181990
risk_code
36/37/38-41-37/38-22
化審法
(2)-1369
hazard_code
Xi,Xn
safety_code
26-36/37/39-39

化学と産業

薬理情報

Cellular LocationsCytoplasm
Metabolite PathwaysMalonic Aciduria

用途と製造

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
応用分野 · 4 件

解説3-ヒドロキシプロピオン酸,ヒドロキシプロピオンサン,3-hydroxypropanoic acid.C3H6O3(90.08).HOCH2CH2COOH.ヒドロアクリル酸ともいう.3-ヒドロキシプロピオニトリルの加水分解で得られる.粘ちゅうな液体.pKa1 4.49(30 ℃).水,エタノールに可溶.蒸留または硫酸脱水によりアクリル酸になる.酸化により,シュウ酸と二酸化炭素を生成する.生体内では,プロピオニルCoAカルボキシラーゼの欠損時に,プロピオニルCoAから生成し,さらに酵素作用を受けて,アセチルCoAになる.

用途アクリル酸の合成

説明3-Hydroxypropionic acid (3-HP) is considered as a potential building block either for organic synthesis or high performance polymers.It is a 3-carbon carboxylic acid, structural isomer of lactic acid, which naturally exists in some thermophilic archaea and bacteria. This organic compound has been pointed out by the US Department of Energy as a promising biomass derivate, which could potentially be used for the production of high added-value chemicals like1,3-propanediol, acrylic acid, acrylamide, and bioplastics. Being 3-HP a commercially valuable, important platform chemical, researches have been conducted about its production on commercial scale, mainly from renewable sources. The biological production of 3-HP from glycerol and glucose, both based on microbial fermentation, are among the main routes studied. More specifically, research activities have been devoted to goals such as identifying novel biochemical pathways, metabolic engineering of microbial strains for the production of 3-HP, and improvements of cultivation techniques to increase 3-HP production titers. Despite intense research efforts, there are still important bottlenecks for cost efficient, large scale biological production of 3-Hydroxypropionic Acid.

使用A three carbon non-chiral compound, 3-Hydroxypropionic acid can be used as a building block for industrial chemicals.

調製方法

合成方法グルコースからピルビン酸,アラニンを経て合成

サプライヤー50 社

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]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
成都市久鼎化学技术有限公司18584079237 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

補足説明

定義ChEBI: A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.

関連反応

37 件

関連ノート

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