beta-Hydroxyisovaleric acid

Base Information

• Chemical Name: beta-Hydroxyisovaleric acid
• CAS No.: 625-08-1
• Molecular Formula: C5H10O3
• Molecular Weight: 118.133
• Hs Code.: 29181990
• UNII: 3F752311CD
• DSSTox Substance ID: DTXSID20211535
• Nikkaji Number: J100.466B
• Wikipedia: Beta-Hydroxy_beta-methylbutyric_acid
• Wikidata: Q223081
• NCI Thesaurus Code: C26656
• Metabolomics Workbench ID: 1512
• ChEMBL ID: CHEMBL4303793
• Mol file: 625-08-1.mol

Synonyms:3-hydroxyisovaleric acid;beta hydroxy beta methylbutyrate;beta-hydroxy beta-methylbutyrate;beta-hydroxy-beta-methylbutyrate;beta-hydroxyisovaleric acid;HMB-d6

Chemical Property of beta-Hydroxyisovaleric acid

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 0.00567mmHg at 25°C
• Melting Point: -80 °C(lit.)
• Refractive Index: n20/D 1.4415(lit.)
• Boiling Point: 242.8 °C at 760 mmHg
• PKA: 4.38±0.10(Predicted)
• Flash Point: 114.9 °C
• PSA: 57.53000
• Density: 1.144 g/cm³
• LogP: 0.23200
• Storage Temp.: Refrigerator
• Water Solubility.: Soluble in water and ethanol.
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 118.062994177
• Heavy Atom Count: 8
• Complexity: 95.8

Purity/Quality:

99% ^*data from raw suppliers

β-Hydroxyisovaleric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(CC(=O)O)O
• Recent ClinicalTrials: Spine and Tumor Screening and Supplementation
• Description: 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.
• Uses: 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. 3-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.

Technology Process of beta-Hydroxyisovaleric acid

There total 51 articles about beta-Hydroxyisovaleric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

ethyl 3-hydroxy-3-methylbutanoate (18267-36-2) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Guidance literature:

With water; sodium hydroxide; at 20 ℃;

Reference yield: 91.0%

6,6-dimethyl-4-oxo-2-phenyl-[1,3]oxazinane-3-carboxylic acid tert-butyl ester → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Guidance literature:

With lithium hydroxide; water; In ethanol; at 20 ℃; for 3h;

DOI:10.1055/s-1999-2926

Reference yield: 54.0%

C11H16NO2(1+)*I(1-) → 3-Hydroxy-3-methylbutyric acid (625-08-1)

Guidance literature:

C₁₁H₁₆NO₂⁽¹⁺⁾*I^(1-); With sodium hydroxide; In water; at 90 ℃; for 1h;

With hydrogenchloride; In water;

upstream raw materials:

4,4-dimethyloxetan-2-one

3-methylbutyric acid

2-methylpent-4-en-2-ol

chloroform

Downstream raw materials:

3-Methylbutenoic acid

tert-butyl alcohol

ethyl 3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-1-thio-β-D-glucopyranoside

3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-(3-hydroxy-3-methylbutanamido)-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Refernces

• 1、 -. "Preparation method of calcium [beta]-hydroxy-[beta]-methylbutyrate". . . Retrieved 2020/07/24.
• 2、 -. "SUBSTITUTED HETEROARYL COMPOUNDS AND METHODS OF USE". Paragraph 000642. . Retrieved 2019/06/05.