HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Brenztraubensure
2-OXOPROPANOIC ACID · Propanoic acid, 2-oxo- · pyruvic · FEMA 2970 · CH3COCOOH · 2-oxo-propanoicaci · NSC 179 · PYRUVIC ACID
Identifikatoren & physikalische Daten
| CAS No. | 127-17-3 |
|---|---|
| Summenformel | C3H4O3 |
| Durchschnittliche Molmasse | 88,06 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | Brenztraubensure |
Chemische & physikalische Eigenschaften
| XLogP | -0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 54,4 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 84 |
| Stoffklassen | Biological Agents -> Other Biomolecules |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106] |
| SpringerMaterials Properties | Coriolis coupling |
| Duftstoffe | Fragrance Ingredient (Pyruvic acid) -> IFRA transparency List |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 1.260-1.2811.267 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | 1000.0 mg/mLmiscible with watersoluble in organic solvents, oilsmiscible at room temperature (in ethanol)Miscible with chloroform and methanol.H2O: misciblealcohol: misciblediethyl ether: miscible |
| Siedepunkt | 164 °C165 °C (lit.) |
| Schmelzpunkt | 13.8 °C11-12 °C (lit.) |
| Dampfdruck | 1.29 [mmHg]1.72hPa at 25℃ |
| FEMA | 2970 | PYRUVIC ACID |
| Brechungsindex | n20/D 1.428(lit.) |
| Flammpunkt | 183 °F |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 2.39(at 25℃) |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to light yellow or amber |
| Geruch | at 1.00 % in propylene glycol. sharp sour acetic caramellic |
| pH | 3.11(1 mM solution)2.38(10 mM solution)1.79(100 mM solution) |
| Geruchsart | acidic |
| Biologische Quelle | synthetic |
| JECFA Number | 936 |
| Merck | 14,8021 |
| BRN | 506211 |
| Henry-Konstante | 3.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. Refrigerate. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCE |
| InChI | 1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) |
| InChIKey | LCTONWCANYUPML-UHFFFAOYSA-N |
| SMILES | CC(=O)C(O)=O |
| LogP (Verteilungskoeffizient) | -1.24 |
| CAS Datenbank | 127-17-3(CAS DataBase Reference) |
| NIST chemische Informationen | Pyruvic acid(127-17-3) |
| EPA chemische Informationen | Propanoic acid, 2-oxo- (127-17-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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. |
|---|---|
| Regulatorische Informationen | 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 |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | 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%) |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| Expositionspfade | Pyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation. |
| Toxizitätsübersicht | 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 Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3265 8/PG 2 |
| Zollcode | 29335995 |
| RTECS-Nr. | UZ0829800 |
| R-Sätze (R) | 34 |
| Gefahrensymbole | C |
| Sicherheitshinweise (S) | 26-36/37/39-45-25-27 |
| Gefahrenklasse | 8Eye Dam. 1Skin Corr. 1C |
| Verpackungsgruppe | II |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
| Selbstentzündungstemperatur | 305 °C |
Anwendungen & Verwendung
Occurrence
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.
Verwenden
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.
Herstellung & Synthese
synthetische
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.