3-ヒドロキシプロピオン酸
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)
識別子と物理属性
| CAS No. | 503-66-2 |
|---|---|
| 分子式 | C3H6O3 |
| 平均分子量 | 90.08 g/mol |
| 単同位体質量 | 90.03169405 g/mol |
| SMILES | O=C(O)CCO |
| InChIKey | ALRHLSYJTWAHJZ-UHFFFAOYSA-N |
| PubChem CID | 68152 |
| ChEMBL | CHEMBL1205969 |
| ChEBI | CHEBI:33404 |
| EC No. | 207-974-8 |
| DTXSID | DTXSID50198305 |
| 現地名 | 3-ヒドロキシプロピオン酸 |
化学・物理的性質
| XLogP | -1 |
|---|---|
| 極性表面積 | 57.5 |
| 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 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Dielectric constant |
| 融点 | < 25 °C16.8°C (estimate) |
| Physical Description | Solid |
| 沸点 | 212°C (rough estimate) |
| 密度 | 1.066 g/mL at 25 °C |
| 屈折率 | 1.4489 |
| 引火点 | >110° |
| 貯蔵条件 | 2-8°C |
| 溶解度 | エタノール、メタノール、水270.1g/L(25℃) |
| pKa（酸解離定数） | 4.51(at 25℃) |
| 外観・状態 | 無色溶液 |
| 色 | Colorless to Almost colorless |
| 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 | 503-66-2(CAS DataBase Reference) |
化学性质
アクリル酸の前駆体
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.DangerH302 (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. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (88.9%) |
| 健康影響 | 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. |
| 毒性の概要 | 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 Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | WGK 1 |
| 税関コード | 29181990 |
| 危険文句（R） | 36/37/38-41-37/38-22 |
| 化審法 | (2)-1369 |
| 危険表示 | Xi,Xn |
| 安全措置（S） | 26-36/37/39-39 |
| 危険等級 | Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 10 - Combustible liquids |
用途
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.
製法・合成法
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