18294-85-4

Basic information

• Product Name: (2S)-2-hydroxy-hexanedioic acid
• Synonyms: (2S)-2-hydroxy-hexanedioic acid;2-Hydroxyadipic acid;2-Hydroxyhexanedioic acid;2(S)-hydroxyadipic acid;sodium 2-hydroxyhexanedioate
• CAS NO: 18294-85-4
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• EINECS: 162.1406
• Mol File: 18294-85-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 151 °C
• Boiling Point: 401.6°Cat760mmHg
• Flash Point: 210.8°C
• Appearance: /
• Density: 1.413g/cm³
• Vapor Pressure: 4.04E-08mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: 2-8°C
• Solubility: Methanol, Water
• PKA: 3.77±0.21(Predicted)
• CAS DataBase Reference: (2S)-2-hydroxy-hexanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-hydroxy-hexanedioic acid(18294-85-4)
• EPA Substance Registry System: (2S)-2-hydroxy-hexanedioic acid(18294-85-4)

Safety Data

• Hazardous Substances Data: 18294-85-4(Hazardous Substances Data)

Usage

Description

(2S)-2-hydroxy-hexanedioic acid, also known as 2-hydroxyhexanedioic acid, is an adipic acid derivative with a 2-hydroxy substituent. It is an organic compound that plays a significant role in various chemical and biological processes.

Uses

Used in Chemical Synthesis:
(2S)-2-hydroxy-hexanedioic acid is used as an intermediate in the synthesis of 2-Hydroxyhexanedioic Acid Disodium Salt (H943015). (2S)-2-hydroxy-hexanedioic acid is essential for the production of various chemical products and has potential applications in the pharmaceutical and chemical industries.
Used in Medical Diagnostics:
(2S)-2-hydroxy-hexanedioic acid is used as a biomarker for the detection of 2-ketoadipic acidemia, a rare metabolic disorder. The accumulation and excretion of 2-hydroxyhexanedioic acid (along with 2-ketoadipic and 2-aminoadipic acids) in urine can indicate the presence of this condition, which is caused by a deficiency of 2-ketoadipic dehydrogenase. This application is particularly relevant in the medical and diagnostic industries.

InChI:InChI=1/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)

Upstream product

• 22418-75-3 2-chlorohexane-1,6-dioic acid 
• 3269-62-3 2-bromohexanedioic acid,6-ethyl ester 
• 18294-84-3 2-acetoxy-adipic acid diethyl ester 
• 98-98-6 2-Picolinic acid 
• 7209-06-5 2-chloro-adipic acid diethyl ester 
• 4845-05-0 cyclohex-2-enyl hydroperoxide 
• 7209-01-0 diethyl 2-bromoadipate 
• 19856-36-1 2-chloro-adipic acid dimethyl ester 
• 3184-35-8 2-oxohexanedioic acid 
• 930-68-7 cyclohexenone 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 822-67-3 Cyclohex-2-enol 
• 106-69-4 hexane-1,2,6-triol 
• 3238-40-2 furan-2,5-dicarboxylic acid 

Downstream Products

• 124-04-9 Adipic acid 

Relevant articles and documents

Catalytic transformation of 2,5-furandicarboxylic acid to adipic acid over niobic acid-supported Pt nanoparticles

The conversion of biomass-derived molecules into adipic acid represents a highly attractive green route for sustainable production of adipic acid, a key monomer of nylon 66 and polyurethane. Here, we report the direct synthesis of adipic acid from 2,5-furandicarboxylic acid, which can be obtained from cellulose-based 5-hydroxymethylfurfural, using a niobic acid-supported platinum catalyst under hydrogen in water.

Acidic pH is a metabolic switch for 2-Hydroxyglutarate generation and signaling

2-Hydroxyglutarate (2-HG) is an important epigenetic regulator, with potential roles in cancer and stem cell biology. The D-(R)-enantiomer (D-2-HG) is an oncometabolite generated from α-ketoglutarate (α-KG) by mutant isocitrate dehydrogenase, whereas L-(S)-2-HG is generated by lactate dehydrogenase and malate dehydrogenase in response to hypoxia. Because acidic pH is a common feature of hypoxia, as well as tumor and stem cell microenvironments, we hypothesized that pH may regulate cellular 2-HG levels. Herein we report that cytosolic acidification under normoxia moderately elevated 2-HG in cells, and boosting endogenous substrate α-KG levels further stimulated this elevation. Studies with isolated lactate dehydrogenase-1 and malate dehydrogenase-2 revealed that generation of 2-HG by both enzymes was stimulated severalfold at acidic pH, relative to normal physiologic pH. In addition, acidic pH was found to inhibit the activity of the mitochondrial L-2-HG removal enzyme L-2-HG dehydrogenase and to stimulate the reverse reaction of isocitrate dehydrogenase (carboxylation of α-KG to isocitrate). Furthermore, because acidic pH is known to stabilize hypoxia-inducible factor (HIF) and 2-HG is a known inhibitor of HIF prolyl hydroxylases, we hypothesized that 2-HG may be required for acid-induced HIF stabilization. Accordingly, cells stably overexpressing L-2-HG dehydrogenase exhibited a blunted HIF response to acid. Together, these results suggest that acidosis is an important and previously overlooked regulator of 2-HG accumulation and other oncometabolic events, with implications for HIF signaling.

METHOD FOR SYNTHESIS OF KETO ACID OR AMINO ACID BY HYDRATION OF ACETHYLENE COMPOUND

An object of the present invention is to provide a method for synthesis of keto acids by hydration of an acetylene compound (acetylene-carboxylic acids) under mild conditions free from harmful mercury catalysts and a method for synthesis of amino acids from acetylene-carboxylic acids in a single container (one-pot or tandem synthesis). In one embodiment of the method according to the present invention for synthesis of keto acids, acetylene-carboxylic acids is hydrated in the presence of a metal salt represented by General Formula (1), where M1 represents an element in Group VIII, IX, or X of the periodic table, and X1, X2, or X3 ligand represents halogen, H2O, or a solvent molecule, and k represents a valence of a cation species, and Y represents an anion species, and L represents a valence of the anion species, and each of K and L independently represents 1 or 2, and k × m = L × n.