3-Hydroxyisovaleric acid

HCID 69362CAS 625-08-1

Basic information

Standard SMILES
CC(C)(O)CC(=O)O
InChIKey
AXFYFNCPONWUHW-UHFFFAOYSA-N
Molecular formula
C5H10O3
Average molar mass
118.13 g/mol
Monoisotopic mass
118.06299418

Names & identifiers

Preferred name
3-Hydroxyisovaleric acid
IUPAC
3-hydroxy-3-methylbutanoic acid
English name
beta-Hydroxyisovaleric Acid
Molecular formula
C5H10O3
Molecular weight
118.13

Names & synonyms

beta-Hydroxyisovaleric acid625-08-13-Hydroxy-3-methylbutanoic acid3-Hydroxyisovaleric acid3-Hydroxy-3-methylbutyric acid3-OH-isovaleric acid3-hydroxy-3-methyl-butanoic acid3-hydroxy-isovaleric acidHmb-d6beta-Hydroxy-methylbutyratebeta-hydroxy-beta-methylbutyric acidDTXSID20211535
Show more names
3-HYDROXY-3-METHYL BUTYRIC ACIDβ-Hydroxyisovaleric AcidRARECHEM AL BO 2324HYDROXY-METHYLBUTYRATE3-hydroxyisovalericaci?Hydroxyisovaleric acid
3F752311CDCHEBI:37084RefChem:911412beta hydroxy beta methylbutyratebeta-hydroxy beta-methylbutyrateDTXCID50134026626-699-8B-hydroxyisovaleric acid

Database identifiers

CAS
625-08-1
PubChem CID
69362
DTXSID
DTXSID20211535
ChEMBL
CHEMBL4303793
ChEBI
CHEBI:37084
UNII
3F752311CD
EC Number
626-699-8
Nikkaji
J100.466B

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
2
Heavy atoms
8

Experimental & physicochemical properties

LogP6.300
Melting Point65 - 67 °C
Physical DescriptionSolid
Kovats Retention Index985.2

Physicochemical properties

Melting point
-80 °C · -80 °C (lit.)
Boiling point
88 °C/1 · 88 °C/1 mmHg (lit.)
Density
0.938 g/mL · 0.938 g/mL at 25 °C (lit.)
refractive index
20 · n20/D 1.4415(lit.)
Flash point
113 °C · 113 °C
storage temp.
Keep in dark place,Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H315 (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 exposure; Respiratory 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 information

Hazard Classes and CategoriesSkin Irrit. 2 (100%);Eye Irrit. 2 (100%);STOT SE 3 (97.9%)

Toxicology

Health Effects · 1 item

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.

Toxicity Summary · 1 item

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

Safety data

F
10-13-21
PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
ridadr
UN 3334
hs_code
29181990
risk_code
36/37/38

Chemistry & industry

Pharmacology

Tissue LocationsFibroblasts;Placenta
Cellular LocationsCytoplasm

Uses & manufacturing

UsesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Applications · 3 items

Descriptionβ-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.

Usesβ-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.

Uses3-Hydroxy-3-methylbutyric acid is a useful biochemical for synthesis and proteomics research. It is used as an indicator of biotin deficiency. Further, it is used to increase muscle mass and decrease muscle breakdown. In addition to this, it is involved in the protein synthesis.

Upstream & downstream products

Downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Additional notes

DefinitionChEBI: A 3-hydroxy monocarboxylic acid that is isovaleric acid substituted at position 3 by a hydroxy group. Used as indicator of biotin deficiency.

Related reactions

37 records

Linked notes

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