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
名称をさらに表示
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
- 形式電荷
- 0
- 複雑度
- 50
実験および物理化学的性質
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
- 溶解性
- エタノール、メタノール、水
- 酸解離定数(Pka)
- 4.51 · 4.51(at 25℃)
- 外見
- 無色溶液
- 色
- Colorless to Almost colorless
- 水溶解度
- 270.1 g/L · 270.1g/L(25℃)
- 化粧品成分の機能
- スキンコンディショニング - その他
- InChI
- InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
- InChIKey
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N
- SMILES
- C(O)(=O)CCO
- CAS データベース
- 503 · 503-66-2(CAS DataBase Reference)
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
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
毒性情報
Health Effects
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
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)
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
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2STOT SE 3
- ストレージクラス
- 10 - Combustible liquids
化学と産業
薬理情報
用途と製造
応用分野
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
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
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
関連ノート
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