20312-37-2

Basic information

• Product Name: (R)-2-HYDROXY-4-METHYLPENTANOIC ACID
• Synonyms: D-ALPHA-HYDROXYISOCAPROIC ACID;(R)-2-HYDROXY-4-METHYLPENTANOIC ACID;(2R)-2-hydroxy-4-methylpentanoic acid;D-Leucic acid;D-2-Hydroxy-4-methylpentanoic acid;D-a-Hydroxyisocaproic acid;(R)-Leucic acid;(2R)-2-hydroxy-4-methyl-valeric acid
• CAS NO: 20312-37-2
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• Product Categories: pharmacetical;API intermediates
• Mol File: 20312-37-2.mol
• Article Data: 33

Chemical Properties

• Melting Point: 76-80℃
• Boiling Point: 673.6°Cat760mmHg
• Flash Point: 375.2°C
• Appearance: /
• Density: 1.763g/cm³
• Vapor Pressure: 0.00324mmHg at 25°C
• Refractive Index: 1.457
• Storage Temp.: -15°C
• CAS DataBase Reference: (R)-2-HYDROXY-4-METHYLPENTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-HYDROXY-4-METHYLPENTANOIC ACID(20312-37-2)
• EPA Substance Registry System: (R)-2-HYDROXY-4-METHYLPENTANOIC ACID(20312-37-2)

Safety Data

• Hazardous Substances Data: 20312-37-2(Hazardous Substances Data)

Usage

Description

(R)-2-HYDROXY-4-METHYLPENTANOIC ACID, also known as the (R)-enantiomer of 2-hydroxy-4-methylpentanoic acid, is an organic compound that has been identified in patients with short-bowel syndrome, an inborn error of metabolism, and in maple syrup urine disease (MSUD). It is characterized by its unique molecular structure, which plays a role in its biological functions and interactions.

Uses

Used in Medical Applications:
(R)-2-HYDROXY-4-METHYLPENTANOIC ACID is used as a biomarker for the diagnosis and monitoring of patients with short-bowel syndrome and maple syrup urine disease. Its presence in these conditions helps medical professionals identify the specific metabolic disorders and develop appropriate treatment plans.
Used in Pharmaceutical Research:
(R)-2-HYDROXY-4-METHYLPENTANOIC ACID is used as a compound of interest in pharmaceutical research, particularly in the development of therapies for metabolic disorders. Its unique properties and interactions with biological systems make it a promising candidate for further investigation and potential drug development.
Used in Metabolic Disorder Research:
(R)-2-HYDROXY-4-METHYLPENTANOIC ACID is used as a key molecule in the study of metabolic disorders, such as short-bowel syndrome and maple syrup urine disease. Understanding its role in these conditions can provide insights into the underlying mechanisms and contribute to the development of targeted treatments.
Used in Nutritional Science:
(R)-2-HYDROXY-4-METHYLPENTANOIC ACID is used as a component in the study of nutritional science, particularly in the context of maple syrup urine disease. Research on this compound can help improve our understanding of the role of specific nutrients in metabolism and their impact on overall health.
Used in Analytical Chemistry:
(R)-2-HYDROXY-4-METHYLPENTANOIC ACID is used as a target analyte in analytical chemistry, where its detection and quantification can aid in the diagnosis and monitoring of metabolic disorders. The development of accurate and sensitive methods for its analysis is crucial for advancing our ability to study and treat these conditions.

InChI:InChI=1/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1

Upstream product

• 16979-05-8 isobutyl glyoxal 
• 328-38-1 (R)-leucine 
• 61-90-5 L-leucine 
• 59983-76-5 (R)-6-methyl-hept-2c-en-4-ol 
• 40348-72-9 2-hydroxy-4-methylvaleric acid methyl ester 
• 4502-00-5 sodium 4-methyl-2-oxovalerate 
• 19892-92-3 D-Hyicap-OtBu 
• 89426-79-9 (1S,2S,6R,7R)-4-(1-Methoxymethoxy-3-methyl-butyl)-1,10,10-trimethyl-3-oxa-5-aza-tricyclo[5.2.1.0^2,6]dec-4-ene 
• 816-66-0 4-methyl-2-oxopentanoic acid 
• 13748-90-8 (S)-2-hydroxyl-3,3-dimethylbutyric acid 
• 590-86-3 isovaleraldehyde 
• 56830-23-0 1,1-diethoxy-4-methyl-pentan-2-one 
• 1342309-23-2 trichodepsipeptide A 
• 1342309-24-3 trichodepsipeptide B 

Downstream Products

• 60856-83-9 (R)-ethyl 4-methyl-2-hydroxypentanoate 
• 40348-72-9 2-hydroxy-4-methylvaleric acid methyl ester 
• 73604-32-7 D-α-hydroxyisocaproyl-Leu-Val-Phe-OCH3 
• 37755-48-9 benzyl (R)-2-hydroxy-4-methylpentanoate 
• 58455-94-0 (R)-2-Hydroxy-4-methyl-pentanoic acid 4-nitro-benzyl ester 
• 112529-90-5 (R)-methyl 2-hydroxy-4-methylpentanoate 
• 168069-99-6 Diphenylmethyl (2R)-2-hydroxy-4-methylpentanoate 
• 87760-51-8 4-methyl-1,2-pentanediol 
• 187753-73-7 (S)-1-((R)-2-Hydroxy-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 178977-41-8 (2S)-2-[3-[(2R)-2-(tert-butoxycarbonylamino)-3-(4-methoxyphenyl)propanoylamino]propanoyloxy]-4-methylpentanoic acid 
• 746579-48-6 2-(9H-fluoren-9-ylmethoxycarbonyloxy)-4-methyl-pentanoic acid 
• 130317-28-1 benzyl 2R-trifluoromethanesulfonyloxy-4-methylvalerate 
• 219616-31-6 2-(tert-butoxycarbonyl)-(3R)-3-isobutylsuccinic acid 
• 184948-24-1 tert-butyl (2R)-1,2-dibenzyl 4-methylpentane-1,1,2-tricarboxylate 

Relevant articles and documents

Synthesis of 2-hydroxy acid from 2-amino acid by Clostridium butyricum

Cultures of Clostridium butyricum type strain in synthetic medium supplemented with various L-2-amino acids revealed the presence of the corresponding 2-hydroxy acid. This metabolite is able to produce the polyester poly(2-hydroxyalkanoic acid). The bioconversion is not stereoselective since D-2-amino acids were also converted. Chiral GC analysis demonstrated that only D-enantiomer is formed from L-leucine.

Efficient Synthesis of D-Phenylalanine from L-Phenylalanine via a Tri-Enzymatic Cascade Pathway

D-phenylalanine is an important intermediate in food and pharmaceutical industries. Here, to enable efficient D-phenylalanine biosynthesis from L-phenylalanine, a tri-enzymatic cascade was designed and reconstructed in vivo. The activity of Proteus vulgaris meso-diaminopimelate dehydrogenase (PvDAPDH) toward phenyl pyruvic acid was identified as the limiting step. To overcome, the tension in the phenyl pyruvic acid side-chain, PvDAPDH was engineered, generating PvDAPDHW121A/R181S/H227I, whose catalytic activity of 6.86 U mg?1 represented an 85-fold increase over PvDAPDH. Introduction of PvDAPDHW121A/R181S/H227I, P. mirabilis L-amino acid deaminase, and Bacillus megaterium glucose dehydrogenase in E. coli enabled the production of 57.8 g L?1 D-phenylalanine in 30 h, the highest titer to date using 60 g L?1 L-phenylalanine as starting substrate, which meant a 96.3 % conversion rate and >99 % enantioselectivity on a 3-L scale. The proposed tri-enzymatic cascade provides a novel potential bio-based approach for industrial production of D-phenylalanine from cheap amino acids.

Medusamide a, a panamanian cyanobacterial depsipeptide with multiple β-amino acids

From a collection of marine cyanobacteria made in the Coiba National Park along the Pacific coast of the Republic of Panama a novel cyclic depsipeptide, given the trivial name medusamide A, has been isolated and fully characterized. Medusamide A contains four contiguous β-amino acid (2R,3R)-3-amino-2-methylhexanoic acid (Amha) residues. This is the first report of multiple Amha residues and contiguous β-amino acid residues within a single cyclic peptide-type natural product. Stereochemical assignment of the Amha residues was completed following the synthesis of reference standards for this β-amino acid and the subsequent derivatization with Marfey's reagent and LC-MS analysis.