Pyruvic Acid (HCID 1060)

概要

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.

名称と識別子

優先名称: Pyruvic Acid
IUPAC: 2-oxopropanoic acid
現地名: ピルビン酸
英語名: Pyruvic acid
分子式: C3H4O3
分子量: 88.06

名称と別名

Pyruvic acid2-Oxopropanoic acid127-17-3acetylformic acidPyroracemic acid2-Oxopropionic acidPropanoic acid, 2-oxo-alpha-ketopropionic acid2-Ketopropionic acid2-Oxopropansaeure2-Oxopropionsaeurealpha-Oxopropionsaeure

名称をさらに表示

ピルビン酸2-オキソプロピオン酸2-オキソプロパン酸2-ケトプロピオン酸焦性ぶどう酸アセチルぎ酸ピルビンピルビン酸, 98%ピルビン酸 98%pyruvicFEMA 29702-oxo-propanoicaciNSC 179Pyruvia AcidACID PYRUVATE

2-oxo-propionic acidacide pyruviquea-Ketopropionic acidCH3COCOOHFEMA No. 2970BrenztraubensaeureDTXSID2021650NSC-179

データベース識別子

CAS: 127-17-3
PubChem CID: 1060
DTXSID: DTXSID2021650
ChEBI: CHEBI:32816
UNII: 8558G7RUTR
EC Number: 204-824-3
Nikkaji: J2.015J

物性

構造計算による物性

XLogP: -0.3
極性表面積: 54.4 Å²
水素結合供与体数: 1
水素結合受容体数: 3
回転可能結合数: 1
重原子数: 6
形式電荷: 0
複雑度: 84

実験および物理化学的性質

Chemical ClassesBiological Agents -> Other Biomolecules

DrugsPharmaceuticals -> Listed in ZINC15

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106]

SpringerMaterials PropertiesCoriolis coupling

FragrancesFragrance Ingredient (Pyruvic acid) -> IFRA transparency List

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

物理化学的性質

融点: 11 · 11-12 °C (lit.)
沸点: 165 °C · 165 °C (lit.)
比重(密度): 1.267 g/mL · 1.267 g/mL at 25 °C (lit.)
蒸気圧: 1.72 hPa · 1.72hPa at 25℃
FEMA: 2970 · 2970 | PYRUVIC ACID
屈折率: 20 · n20/D 1.428(lit.)
闪点: 183 °F · 183 °F
貯蔵温度: 2 · 2-8°C
溶解性: クロロホルムおよびメタノールと混和します。
酸解離定数(Pka): 2.39 · 2.39(at 25℃)
外見: 液体
色: 無色透明～薄黄色または琥珀色
臭い (Odor): 1 %。シャープな酸味の酢酸キャラメル · プロピレングリコール中1.00%。シャープな酸味の酢酸キャラメル
PH: 3.11 · 3.11(1 mM solution);2.38(10 mM solution);1.79(100 mM solution);
においのタイプ: 酸性の
由来生物: synthetic
水溶解度: 2 O: · H2O: misciblealcohol: misciblediethyl ether: miscible
JECFA Number: 936 · 936
Merck: 14 · 14,8021
BRN: 506211 · 506211
Henry's Law Constant: 3.1 · 3.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
安定性: 安定。可燃性。強酸化剤、強塩基とは相容れない。冷蔵します。
主な用途: フレーバーそして香料
化粧品成分の機能: 香料
InChI: 1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
InChIKey: LCTONWCANYUPML-UHFFFAOYSA-N
SMILES: CC(=O)C(O)=O
LogP: -1.24 · -1.24
CAS データベース: 127 · 127-17-3(CAS DataBase Reference)
NISTの化学物質情報: Pyruvic acid(127-17-3)
EPAの化学物質情報: 2 · Propanoic acid, 2-oxo- (127-17-3)

化学的性質

化学的特性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

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 4 件

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

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

Hazards Summary · 1 件

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]

Hazard Classes and CategoriesSkin Corr. 1B (100%)

毒性情報

Adverse EffectsDermatotoxin - Skin burns.

Exposure RoutesPyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation.

Toxicity Summary · 1 件

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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk: 3
tsca: TSCA listed
rtecs: UZ0829800
ridadr: UN 3265 8/PG 2
hs_code: 29335995
risk_code: 34
化審法: (2)-959, (2)-1473
消防法: 危-4-3-III
hazard_code: C
safety_code: 26-36/37/39-45-25-27
hazard_class: 8
packing_group: II
自然発火温度: 305 °C
Hazard Classifications: Eye Dam. 1Skin Corr. 1C
ストレージクラス: 8A - Combustible corrosive hazardous materials

化学と産業

薬理情報

Pharmacodynamics · 1 件

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 · 1 件

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 · 2 件

In the liver, pyruvate is metabolized via several pathways.

Absorption, Distribution and ExcretionPyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation.

Tissue LocationsAdipose Tissue

Cellular LocationsExtracellular

用途と製造

Uses · 2 件

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 · 6 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationPropanoic acid, 2-oxo-: ACTIVE

応用分野 · 5 件

解説ピルビン酸，焦性ブドウ酸ともいう．生体内の物質代謝過程での重要な中間体で，アラニンの前駆物質とも考えられる．シアン化アセチルを加水分解するか，酒石酸またはブドウ酸を硫酸水素ナトリウムと加熱すると得られる．酢酸臭のある液体．融点13.6 ℃，沸点165 ℃(分解)，58 ℃(1.3 kPa)．d415"1.267．nD20"1.4138．K 3.2×10－3(25 ℃)．水，エタノール，エーテルに易溶．還元するとD,L-乳酸になる．濃硫酸と加温すると容易に一酸化炭素を放って酢酸となる．有機合成反応，重火傷の軟膏などに用いられる．

天然物の起源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.

使用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.

一般的な説明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.

使用用途ピルビン酸の使用用途として、生物学実験での試薬が挙げられます。ピルビン酸は生物のエネルギー供給に重要な役割を果たすだけでなく、からピルビン酸へのアミノ基転位により、アミノ酸の1種であるアラニンを産生します。このようにピルビン酸は、アミノ酸、タンパク質、ATP合成など、生物の生体内反応に極めて重要な化合物です。そのためピルビン酸は、細胞や微生物を培養するために用いられています。具体例として、ピルビン酸は、ピルビン酸ナトリウムとして細胞培養液の材料や細胞培養液の添加物として使用されています。また、ピルビン酸はヒトにとって欠かせない栄養素です。そのため、サプリメントなどにも含まれていることもあります。ピルビン酸をメチル化して合成できるピルビン酸メチルは、香料などとして食品添加物に使用されることがあります。ピルビン酸メチルは水中でピルビン酸に加水分解されるため、摂取しても危険性はないとされています。

調製方法 · 2 件

製造方法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.

純化方法Distil it twice, then fractionally crystallise it by partial freezing. [Beilstein 3 IV 1505.]

上流・下流製品情報

上流原料

下流製品

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補足説明 · 2 件

定義本品は、次の化学式で表される有機酸である。

定義Pyruvic acid is an important organic chemical intermediate, an intermediate compound in the metabolism of carbohydrates, proteins, and fats, and is used in a variety of fields, including the pharmaceutical, cosmetic, food, and chemical industries. It has roles as a basic metabolite and cofactor. In thiamine deficiency, its oxidation is retarded and it tends to accumulate in neurostructural tissues causing neurological damage. In vitro studies have shown that pyruvic acid modulates cardiac function at physiological or low doses, but can cause cardiomyocyte damage at high doses.

ピルビン酸

基本情報

概要