3-Hydroxyisovaleric acid
3-Hydroxyisovaleric acid · 3-HYDROXY-3-METHYLBUTANOIC ACID · 3-HYDROXY-3-METHYL BUTYRIC ACID · β-Hydroxyisovaleric Acid · BETA-HYDROXY BETA-METHYLBUTYRATE · RARECHEM AL BO 2324 · 3-OH-isovaleric acid · HYDROXY-METHYLBUTYRATE
Identifikatoren & physikalische Daten
| CAS No. | 625-08-1 |
|---|---|
| Summenformel | C5H10O3 |
| Durchschnittliche Molmasse | 118,13 g/mol |
| Monoisotopische Masse | 118,06299418 g/mol |
| SMILES | CC(C)(O)CC(=O)O |
| InChIKey | AXFYFNCPONWUHW-UHFFFAOYSA-N |
| PubChem CID | 69362 |
| ChEMBL | CHEMBL4303793 |
| ChEBI | CHEBI:37084 |
| EC No. | 626-699-8 |
| DTXSID | DTXSID20211535 |
Chemische & physikalische Eigenschaften
| XLogP | -0,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 57,5 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 95 |
| LogP (Verteilungskoeffizient) | 6.300 |
| Schmelzpunkt | 65 - 67 °C-80 °C (lit.) |
| Physical Description | Solid |
| Kovats Retention Index | 985.2 |
| Siedepunkt | 88 °C/1 mmHg (lit.) |
| Dichte | 0.938 g/mL at 25 °C (lit.) |
| Brechungsindex | n20/D 1.4415(lit.) |
| Flammpunkt | 113 °C |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Löslichkeit | DMF:10.0(Max Conc. mg/mL)84.65(Max Conc. mM)DMSO:10.0(Max Conc. mg/mL)84.65(Max Conc. mM)Ethanol:10.0(Max Conc. mg/mL)84.65(Max Conc. mM)PBS (pH 7.2):10.0(Max Conc. mg/mL)84.65(Max Conc. mM)Soluble in water and ethanol. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 4.38±0.10(Predicted) |
| Wichte | 1.10 |
| Farbe | Pale yellow |
| BRN | 1743952 |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIOXIDANT |
| InChI | 1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7) |
| InChIKey | AXFYFNCPONWUHW-UHFFFAOYSA-N |
| SMILES | CC(C)(O)CC(O)=O |
| CAS Datenbank | 625-08-1(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (97.9%): 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, 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 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.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. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (97.9%) |
| Gesundheitliche Auswirkungen | Chronically high levels of 3-hydroxyisovaleric acid are associated with at least 4 inborn errors of metabolism including: 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency, 3-Methylglutaconic Aciduria Type I, Biotinidase deficiency and Isovaleric Aciduria. |
| Toxizitätsübersicht | 3-Hydroxyisovaleric acid is a normal human metabolite excreted in the urine. Elevated levels of this compound are found in several disorders due to impairment of renal reclamation of biotin. Levels may also be increased from prolonged consumption of raw egg-whites. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| F | 10-13-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 3334 |
| Zollcode | 29181990 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
β-Hydroxy β-methylbutyric acid (HMB), or β-hydroxy β- methylbutyrate, is a metabolite of the essential amino acid leucine and is synthesized in the human body. It plays a part in protein synthesis and was discovered by Dr. Steven L. Nissen at Iowa State University. It has been used in scientific studies to purportedly increase muscle mass and decrease muscle breakdown. Nissen held the original patent on the metabolite as a nutritional supplement. It was discovered in pigs, and small quantities can also be found in grapefruit, alfalfa, and catfish. As a supplement it is usually sold as a calcium salt. Research published in the Journal of Applied Physiology has shown that HMB may have an effect on increasing muscle weight and strength. A review in Nutrition & Metabolism provides an in depth and objective analysis of HMB research. The same study lists as HMB' s proposed mechanisms of action the following: Increased sarcolemmal integrity via conversion to HMG-CoA Enhanced protein synthesis via the mTOR pathway Depression of protein degradation through inhibition of the ubiquitin pathway Three grams of Calcium beta-hydroxy-beta-methylbutyrate per day may help muscles combat protein breakdown, assist in muscle repair and support increased endurance. Studies suggest its benefits may be greater for the untrained. Also, well-controlled scientific studies have found increases in muscle mass and decreases in body fat in 70 year old men. It has helped patients with chronic obstructive pulmonary disease in hospital intensive care units, muscle wasting associated with HIV or AIDS and with cancer, and trauma victims with severe injuries. The human body produces about 0.2 - 0.4 grams per day. Standard doses in research studies have been 1.5 to 3.0 grams per day, usually divided into two doses.
Verwenden
β-Hydroxyisovaleric Acid is a metabolite of the essential amino acid Leucine and is synthesized in the human body. Studies suggest that β-Hydroxyisovaleric Acid may have an effect on increasing muscle weight and strength. The presence of elevated β-Hydroxyisovaleric Acid is a sensitive marker of biotin deficiency and may indicate the presence of a genetic disorder such as biotinidase deficiency or holocarboxylase synthetase deficiency.