DL-酒石酸
DL-酒石酸 · rac-(2R*,3R*)-2,3-ジヒドロキシこはく酸 · ラセミ酸 · rac-(2R*,3R*)-2,3-ジヒドロキシブタン二酸 · (±)-2,3-ジヒドロキシブタン二酸 · (±)-酒石酸 · ラセム酸 · dl酒石酸
識別子と物理属性
| CAS No. | 133-37-9 |
|---|---|
| 分子式 | C4H6O6 |
| 平均分子量 | 150.09 g/mol |
| 単同位体質量 | 150.01643791 g/mol |
| SMILES | O=C(O)C(O)C(O)C(=O)O |
| InChIKey | FEWJPZIEWOKRBE-UHFFFAOYSA-N |
| PubChem CID | 875 |
| ChEMBL | CHEMBL333714 |
| ChEBI | CHEBI:15674 |
| EC No. | 205-105-7 |
| DTXSID | DTXSID501031477 |
| 現地名 | DL-酒石酸 |
化学・物理的性質
| XLogP | -1.9 |
|---|---|
| 極性表面積 | 115 |
| 水素結合供与体数 | 4 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 3 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 134 |
| 溶解度 | soluble in water and alcohol1 gm in 0.8 ml water1 g in 3 ml 95% alcohol (in ethanol)H2O: 0.1 g/mL、透明溶ける |
| Physical Description | White solid[ICSC] Colorless or white odorless solid[JECFA] White odorless crystalline powder[Acros Organics MSDS]colourless or translucent crystals, or a white, fine to granular crystaline powder which is odourless with an acid taste |
| Kovats Retention Index | 1262 |
| Collision Cross Section | 115.46 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]124.4 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 融点 | 210-212 °C(lit.) |
| 沸点 | 191.59°C (rough estimate) |
| 比旋光度 | [α]D20 -0.2～+0.2° (c=20, H2O) |
| 密度 | 1.788 |
| 蒸気圧 | <0.1 hPa (20 °C) |
| FEMA | 3044 | TARTARIC ACID (D-, L-, DL-, MESO-) |
| 屈折率 | 1.5860 (estimate) |
| 引火点 | 210 °C |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| pKa（酸解離定数） | 3.03, 4.37(at 25℃) |
| 色 | 白い |
| pH | 3.19(1 mM solution)2.58(10 mM solution)2.03(100 mM solution) |
| 臭い | 100.00%で。とてもマイルドなキャラメル味 |
| においのタイプ | 無臭 |
| 由来生物 | synthetic |
| Merck | 14,9069 |
| JECFA Number | 621 |
| BRN | 1725148 |
| 誘電率 | 35.9(-10℃) |
| 安定性 | 安定。塩基、酸化剤、還元剤、銀と相容れない。 |
| 主な用途 | フレーバーそして香料 |
| 化粧品成分の機能 | バッファリング香料 |
| InChI | 1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m0/s1 |
| InChIKey | FEWJPZIEWOKRBE-UHFFFAOYSA-N |
| SMILES | O[C@@H]([C@H](O)C(O)=O)C(O)=O |
| LogP（分配係数） | -1.43 |
| CAS データベース | 133-37-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Tartaric acid(133-37-9) |
| EPAの化学物質情報 | Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel- (133-37-9) |
化学的特性
DL-Tartaric acid is a water- and alcohol-soluble colorless crystalline solid with a characteristic acid taste and a melting temperature of 170°C(338°F). Naturally occurring tartaric acid is generally of the L-configuration (based on the absolute configuration of D-glyceric acid). The L-forms of tartrates are dextrorotatory in solution and thus are designated as L(+)-tartrates. It is also known as dihydroxy succinic acid. Tartaric acid is used as a chemical intermediate and a sequestrant,as well as in tanning, effervescent beverages, baking powder, ceramics, photography, textile processing,mirror silvering,and metal coloring.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 5.1% (26 of 506) of reports.DangerH315 (22.1%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (53.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (41.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (15.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, 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 506 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 26 of 506 reports by companies.There are 12 notifications provided by 480 of 506 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Chemical: Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(.+-.)-Status: Active Update: 03-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34095 |
| その他の安全情報 | IMAP assessments - Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(.+-.)-: Human health tier I assessmentEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 有害性の概要 | Causes burnsInhalation of aerosol may cause pulmonary edema[ICSC] An irritant[Acros Organics MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (22.1%)Eye Dam. 1 (53.6%)Eye Irrit. 2 (41.3%)STOT SE 3 (15.4%)Skin Irrit. 2 (100%)Eye Irrit. 2A (100%)STOT SE 3 (100%) |
| 有害作用 | Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 29181200 |
| 危険文句（R） | 36/37/38-41 |
| 化審法 | (2)-1456 |
| 危険表示 | Xi |
| 安全措置（S） | 26-37/39-36 |
| 自然発火温度 | 425 °C |
| 危険等級 | Eye Dam. 1 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
dl－ 酒石酸ともいわれる。化学式 C4H8O8 。旋光性はないが，分割すれば d -酒石酸と l -酒石酸に分けることができる。マンニットを硝酸で酸化すると生成する。またブドウの果汁中に存在することがある。無水塩は無色の結晶 (73℃以上の熱水から再結晶) で，融点 206℃。1水塩の融点 203～204℃。カルシウム，ストロンチウムの定量試薬に使われる。ブリタニカ国際大百科事典 小項目事典 ブリタニカ
天然物の起源
d-Tartaric acid occurs in many fruits or other parts of the plant, free or combined with potassium, calcium or magnesium. It is also reported found in raw, lean fish, white wine, red wine and port wine.
使用
DL-Tartaric acid is used as a synergist for antioxidants, emulsifier, sequestrant and flavoring agent. It is also added with citric acid to prepare effervescent salts, thereby enhancing the taste of oral medications. It is also utilized in pigments, processing aids, ink, toner and colorant products. It acts as a chelating agent in metal and farming industries. Further, it is used as lubricant and grease. It is mixed with sodium bicarbonate and used as a leavening agent in food preparation. In the pharmaceutical industry, it is utilized in the preparation of tartar emetic, which is used in cough syrup as an expectorant.
使用用途
酒石酸は、食品添加物として利用される場合が多いです。爽やかな酸味を与える酸味料あるいは調味料として、清涼飲料水、ゼリー、ジャム、ソースなどに用いられます。また、酒石酸の塩である酒石酸水素カリウムや酒石酸ナトリウムは、加熱すると分解して二酸化炭素を放出する性質を利用して、膨張剤にも使用される場合があります。 そのほか、pHの調整や収れん作用を目的に、化粧品に配合されることも多いです。やと合わせてケミカルピーリング溶剤に入れることで、皮膚の古い角質を除去する効果があると言われています。 また、酒石酸は有機合成における原料や触媒としても用いられています。
製法・合成法
製造方法
The tartrates used in commerce are obtained as a by-product of wine manufacture and have the L(+) configuration. Produced from argols or wine lees, which are formed in the manufacture of wine by extracting the potassium acid tartrate, transforming this into the calcium salt and then acidifying with dilute sulfuric acid; also by oxidation of d-glucose with nitric acid. The dl-tartaric acid is obtained by boiling the d-tartaric acid with an aqueous solution of NaOH or by oxidation of fumaric acid. The l- and the meso-tartaric acid are also known, but are less important.