기본 정보
- CAS
1892-67-7- 표준 SMILES
CC(=O)C(=O)O- InChIKey
LCTONWCANYUPML-UHFFFAOYSA-N- 분자식
- C3H4O3
- 평균 분자량
- 88.06 g/mol
개요
Pyruvic acid is a 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis. It has a role as a cofactor and a fundamental metabolite. It is functionally related to a propionic acid. It is a conjugate acid of a pyruvate.
이름 및 식별자
- 우선 이름
- Pyruvic Acid
- IUPAC
- 2-oxopropanoic acid
- 영어명
- 2-Oxopropanoic acid
- 분자식
- C3H4O3
- 분자량
- 88.06206
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
1892-67-7- ChEBI
CHEBI:32816- UNII
- 8558G7RUTR
- EC Number
- 204-824-3
- Nikkaji
- J2.015J
물성
구조 계산 물성
- XLogP
- -0.3
- 극성 표면적
- 54.4 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 6
- 형식 전하
- 0
- 복잡도
- 84
실험 및 물리화학적 성질
Solubility
1000.0 mg/mL
miscible with water; soluble in organic solvents, oils
miscible at room temperature (in ethanol)
안전 및 규제
GHS 분류
GHS Classification
Danger
H314 (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.
유해성 정보
Regulatory Information
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Commission Regulation (EC) No 1565/2000 (Repealed by Com.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/23815
Pyruvic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
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 burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Sigma-Aldrich MSDS]
독성 정보
Toxicity Summary
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.
화학 및 산업
약리 정보
Pharmacodynamics
Pyruvic acid or pyruvate is a key intermediate in the glycolytic and pyruvate dehydrogenase pathways, which are involved in biological energy production. Pyruvate is widely found in living organisms. It is not an essential nutrient since it can be synthesized in the cells of the body. Certain fruits and vegetables are rich in pyruvate. For example, an average-size red apple contains approximately 450 milligrams. Dark beer and red wine are also rich sources of pyruvate. Recent research suggests that pyruvate in high concentrations may have a role in cardiovascular therapy, as an inotropic agent. Supplements of this dietary substance may also have bariatric and ergogenic applications.
Mechanism of Action
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.
Metabolism/Metabolites
In the liver, pyruvate is metabolized via several pathways.
In the liver, pyruvate is metabolized via several pathways.
용도 및 제조
Uses
Intermediate in sugar metabolism and alcoholic fermentation; [Merck Index] Used as flavoring agent or adjuvant; [FDA]
For nutritional supplementation, also for treating dietary shortage or imbalance
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
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