53585-93-6

Basic information

• Product Name: (R)-(-)-HEXAHYDROMANDELIC ACID
• Synonyms: (R)-(-)-HEXAHYDROMANDELIC ACID;R(-)-CYCLOHEXYLHYDROXYACETIC ACID;ALPHA-HYDROXYCYCLOHEXANE-ACETIC ACID;2-CYCLOHEXYLGLYCOLIC ACID;CYCLOHEXYL-HYDROXY-ACETIC ACID;D-HEXAHYDROMANDELIC ACID;Cyclohexylglycolic acid;hexahydromandelic acid
• CAS NO: 53585-93-6
• Molecular Formula: C₈H₁₄O₃
• Molecular Weight: 158.19
• Mol File: 53585-93-6.mol
• Article Data: 20

Chemical Properties

• Melting Point: 127-129 °C(lit.)
• Boiling Point: 319.3 °C at 760 mmHg
• Flash Point: 161.1 °C
• Appearance: /
• Density: 1.178 g/cm³
• Vapor Pressure: 2.8E-05mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: 2-8°C
• PKA: 3.86±0.11(Predicted)
• BRN: 3196809
• CAS DataBase Reference: (R)-(-)-HEXAHYDROMANDELIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-HEXAHYDROMANDELIC ACID(53585-93-6)
• EPA Substance Registry System: (R)-(-)-HEXAHYDROMANDELIC ACID(53585-93-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 53585-93-6(Hazardous Substances Data)

Usage

Uses

(R)-(?)-Hexahydromandelic acid can be used:As an intermediate in the synthesis of antimycobacterial compound pyridomycin analogs.As a model α-hydroxy acid compound in the chirality sensing studies of organic probes using circular dichroism technique.As a starting material in the synthesis of chiral ionic liquids, which are applicable as chiral solvents in asymmetric synthesis and as chiral stationary phases in chromatographic separations.

Purification Methods

It forms hexagonal clusters on recrystallisation from CCl4 or Et2O. [Wood & Comley J Chem Soc 2638 1924, Lettré et al. Chem Ber 69 1594 1936]. The racemate has m 137.2-137.6o (134-135o) [Smith et al. J Am Chem Soc 71 3772 1949]. [Beilstein R-10 II 5; S-10 II 6.]

InChI:InChI=1/C8H14O3/c9-7(8(10)11)6-4-2-1-3-5-6/h6-7,9H,1-5H2,(H,10,11)/t7-/m1/s1

Upstream product

• 62455-70-3 3-cyclohexyl-3-oxopropanenitrile 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 69455-34-1 rac-2-cyclohexenyl-2-hydroxyethanoic acid 
• 57741-12-5 α-(trichloromethyl)cyclohexanemethanol 
• 157982-33-7 (R)-S-ethylthio cyclohexylglycolate 
• 106975-25-1 ethyl (R)-2-hydroxy-2-cyclohexylacetate 
• 4354-47-6 (R)-2-cyclohexyl-2-hydroxyacetonitrile 
• 611-71-2 (R)-Mandelic Acid 
• 75730-04-0 (dimethylphenylsilyl)-1-cyclohexylmethanol 
• 124-38-9 carbon dioxide 
• 1504663-32-4 [cyclohexyl{(trimethylsilyl)oxy}methyl]dimethylphenylsilane 
• 99183-16-1 rac-methyl 2-cyclohexyl-2-hydroxyacetate 
• 110-83-8 cyclohexene 
• 96312-31-1 -tartronsaeure-diethylester 

Downstream Products

• 99183-16-1 rac-methyl 2-cyclohexyl-2-hydroxyacetate 
• 106975-25-1 ethyl (R)-2-hydroxy-2-cyclohexylacetate 
• 716362-15-1 benzyl 2-cyclohexyl-2-hydroxyethanoate 
• 1033777-80-8 C₁₈H₃₂N₂O₄ 
• 1033777-07-9 2-cyclohexyl-2-hydroxy-N-(4-imidazol-1-ylphenyl)acetamide 
• 92572-85-5 (R)-methyl 2-(benzyloxy)-3-cyclohexylacetate 
• 141692-80-0 (R)-2-(benzyloxy)-2-cyclohexylacetaldehyde 
• 187403-13-0 benzyl (R)-2-cyclohexyl-2-(trifluoromethylsulfonyloxy)acetate 
• 866890-36-0 methyl {2-O-acetyl-4,6-O-benzylidene-3-O-[(S)-1-(benzyloxycarbonyl)(cyclohexyl)methyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 
• 866890-41-7 methyl {2,4,6-tri-O-acetyl-3-O-[(S)-(benzyloxycarbonyl)(cyclohexyl)methyl]-β-D-galactopyranosyl}-(1->3)-2-(acetylamino)-4,6-di-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 866890-31-5 methyl {4,6-O-benzylidene-3-O-[(S)-(benzyloxycarbonyl)(cyclohexyl)methyl]-β-D-galactopyranosyl}-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 

Relevant articles and documents

Selective Monovalent Galectin-8 Ligands Based on 3-Lactoylgalactoside

Galectin-8 has gained attention as a potential new pharmacological target for the treatment of various diseases, including cancer, inflammation, and disorders associated with bone mass reduction. To that end, new molecular probes are needed in order to better understand its role and its functions. Herein we aimed to improve the affinity and target selectivity of a recently published galectin-8 ligand, 3-O-[1-carboxyethyl]-β-d-galactopyranoside, by introducing modifications at positions 1 and 3 of the galactose. Affinity data measured by fluorescence polarization show that the most potent compound reached a KD of 12 μM. Furthermore, reasonable selectivity versus other galectins was achieved, making the highlighted compound a promising lead for the development of new selective and potent ligands for galectin-8 as molecular probes to examine the protein's role in cell-based and in vivo studies.

Asymmetric hydrogenation reaction of alpha-ketoacids compound

The invention relates to the technical field of organic chemistry, especially to an asymmetric hydrogenation reaction of an alpha-ketoacids compound. The asymmetric hydrogenation reaction comprises a scheme shown in the description. In the scheme, R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, C1-C6 alkyl, or aralkyl; a substituent group is C1-C6 alkyl, C1-C6 alkoxy, or halogen; and the number of the substituent group is 1-3. In the scheme, M is a chiral spiro-pyridylamino phosphine ligand iridium complex having a structure shown in the description. In the structure, R is hydrogen, 3-methyl, 4-tBu, or 6-methyl.

Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives

In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.