피루브산
피루브산 · 파이루빅애씨드 · 2-OXOPROPANOIC ACID · Propanoic acid, 2-oxo- · pyruvic · FEMA 2970 · CH3COCOOH · 2-oxo-propanoicaci
식별자 및 물리적 특성
| CAS No. | 127-17-3 |
|---|---|
| 분자식 | C3H4O3 |
| 평균 분자량 | 88.06 g/mol |
| 단동위원소 질량 | 88.01604399 g/mol |
| SMILES | CC(=O)C(=O)O |
| InChIKey | LCTONWCANYUPML-UHFFFAOYSA-N |
| PubChem CID | 1060 |
| ChEBI | CHEBI:32816 |
| EC No. | 204-824-3 |
| DTXSID | DTXSID2021650 |
| 현지명 | 피루브산 |
화학 및 물리적 성질
| XLogP | -0.3 |
|---|---|
| 극성 표면적 | 54.4 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 6 |
| 형식 전하 | 0 |
| 복잡도 | 84 |
| 물질 분류 | Biological Agents -> Other Biomolecules |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| 지질 | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106] |
| SpringerMaterials Properties | Coriolis coupling |
| 향료 | Fragrance Ingredient (Pyruvic acid) -> IFRA transparency List |
| 식품 첨가물 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 밀도 | 1.260-1.2811.267 g/mL at 25 °C (lit.) |
| 향미제 | EU Flavoring substances |
| 용해도 | 1000.0 mg/mLmiscible with watersoluble in organic solvents, oilsmiscible at room temperature (in ethanol)클로로포름 및 메탄올과 혼합 가능. |
| 끓는 점 | 164 °C165 °C (lit.) |
| 녹는점 | 13.8 °C11-12 °C (lit.) |
| 증기압 | 1.29 [mmHg]1.72hPa at 25℃ |
| FEMA | 2970 | PYRUVIC ACID |
| 굴절률 | n20/D 1.428(lit.) |
| 인화점 | 183 °F |
| 저장 조건 | 2-8°C |
| pKa(산도 계수) | 2.39(at 25℃) |
| 물리적 상태 | 액체 |
| 색상 | 무색~담황색 또는 호박색으로 |
| 냄새 | 프로필렌 글리콜 중 1.00%. 날카로운 신맛의 아세트 캐러멜 |
| pH | 3.11(1 mM solution)2.38(10 mM solution)1.79(100 mM solution) |
| 향취 유형 | 산성의 |
| 생물학적 소스 | synthetic |
| 용해도 | H2O: misciblealcohol: misciblediethyl ether: miscible |
| JECFA Number | 936 |
| Merck | 14,8021 |
| BRN | 506211 |
| 헨리 상수 | 3.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| 안정성 | 안정적인. 타기 쉬운. 강한 산화제, 강한 염기와 호환되지 않습니다. 냉장보관하세요. |
| 주요 응용 | 향료 및 향 |
| 화장품 원료 기능 | 향기 |
| InChI | 1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) |
| InChIKey | LCTONWCANYUPML-UHFFFAOYSA-N |
| SMILES | CC(=O)C(O)=O |
| LogP(분배 계수) | -1.24 |
| NIST | Pyruvic acid(127-17-3) |
| EPA | Propanoic acid, 2-oxo- (127-17-3) |
화학적 성질
Pyruvic acid has a sour, acetic odor (similar to acetic acid). It has a pleasant, sour taste with a burning, somewhat sweet note. It tends to darken and decompose unless kept free of minor contaminants and in tightly sealed containers
안전 및 규제
| GHS 분류 | DangerH314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1823 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: Propanoic acid, 2-oxo-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 13-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23815Pyruvic acid: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| 유해성 요약 | Causes degenerative changes to brain in acute cerebral studies of rats[RTECS] Polymerizes and decomposes on standing unless pure and stored in airtight container[Merck Index] Safe when used as a flavoring agent in food[JECFA] Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungs[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Skin Corr. 1B (100%) |
| 유해 작용 | Dermatotoxin - Skin burns. |
| 노출 경로 | Pyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation. |
| 독성 요약 | Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. This inotropic effect is striking in hearts stunned by ischemia/reperfusion. The inotropic effect of pyruvate requires intracoronary infusion. Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. Pyruvate dehydrogenase is inactivated in ischemia myocardium. Yet another is reduction of cytosolic inorganic phosphate concentration. Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione. |
용도
출처
Isolated from cane sugar fermentation broth and from a few plants; also reported found in peppermint, raw asparagus, leaves and stalk of celery, onion, rutabaga, milk, cream, buttermilk, wheaten bread, blue cheeses, cheddar cheese, cottage cheese, provolone cheese, yogurt, beef, Virginia tobacco, beer, white wine, botrytised wine, cocoa and sake.
용도
pyruvic acid is an alpha hydroxy acid that can be irritating and is considered difficult to work with. It has a larger molecular size than the most commonly used AHAs. Sodium pyruvate is more commonly used, and is an organic salt.
일반 설명
Pyruvic acid is the key component formed during the hydrolysis of flavor-precursors called S-alk(en)yl-L-cysteine-sulfoxides in onion tissues by allinase during maceration or chopping. The amount of pyruvic acid formed is used as a measure for onion pungency.
제조 및 합성 방법
제조 방법
By distillation of tartaric acid in the presence of potassium acid sulfate as a dehydrating agent; from acetyl chloride and potassium cyanide to yield the nitrile, which is subsequently acid hydrolyzed to the acid; pyruvic acid must be rectified under vacuum.