54385-47-6

Basic information

• Product Name: D-Mandelic acid sodium salt
• Synonyms: (-)-D-Mandelic acid sodium salt;[R,(-)]-α-Hydroxybenzeneacetic acid sodium salt;D-Mandelic acid sodium salt
• CAS NO: 54385-47-6
• Molecular Formula: C₈H₇O₃*Na
• Molecular Weight: 174.1291
• Mol File: 54385-47-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 321.8°Cat760mmHg
• Flash Point: 162.6°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.00012mmHg at 25°C
• CAS DataBase Reference: D-Mandelic acid sodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: D-Mandelic acid sodium salt(54385-47-6)
• EPA Substance Registry System: D-Mandelic acid sodium salt(54385-47-6)

Safety Data

• Hazardous Substances Data: 54385-47-6(Hazardous Substances Data)

Usage

General Description

D-Mandelic acid sodium salt is a synthetic compound that is derived from mandelic acid, a naturally occurring organic acid found in almond extract and other plant sources. It is commonly used in the pharmaceutical and cosmetic industries for its antiseptic and exfoliating properties. The sodium salt form of D-mandelic acid is typically used as a stabilizer in cosmetic products and as a component of skincare treatments for its ability to enhance the skin's appearance and treat certain dermatological conditions. Additionally, it is used as a chiral building block in the synthesis of pharmaceuticals and other chemical compounds. Due to its diverse applications, D-mandelic acid sodium salt is a widely utilized chemical in various industrial and commercial sectors.

InChI:InChI=1/C8H8O3.Na/c9-7(8(10)11)6-4-2-1-3-5-6;/h1-5,7,9H,(H,10,11);/q;+1/p-1/t7-;/m1./s1

Upstream product

• 43165-51-1 sodium benzoylformate 
• 244223-89-0 (cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate 
• 611-71-2 (R)-Mandelic Acid 

Downstream Products

• 135761-26-1 (S,S)-1,2-Bis<((R)-1'-hydroxy-1'-phenylacetoxy)methyl>-15-krone-5 
• 43165-51-1 sodium benzoylformate 
• 54668-20-1 sodium cyclohexylethanoate 
• 521284-19-5 (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide 

Relevant articles and documents

Structure-cytotoxicity relationship for apoptotic inducers organotin(IV) derivatives of mandelic acid and L-proline and their mixed ligand complexes having enhanced cytotoxicity

Structure-cytotoxicity relationship of di?/tri-organotin(IV) derivatives of mandelic acid (1–4), L-proline (5–7, 15, 16), and mixed ligand complexes of latter with 1,10-phenanthroline (8–14) investigated on the basis of MTT assay against human cancer cell lines, viz. MCF-7 (mammary cancer), HepG2 (liver cancer) and PC-3 (prostate cancer) in vitro indicated that all complexes except methyl- and octyl- analogues displayed potential cytotoxicity. The most active one is dibutyltin(IV) mandelate (2) exhibiting IC50 2.03?±?0.40, 0.98?±?0.23 and 3.86?±?1.68 μM against MCF-7, HepG2 and PC-3, respectively, which is ≈ 15 and 2.5 times against MCF-7, 20 and 5 times against HepG2 and 5 and ≈ 3 times against PC-3 more cytotoxic than cis-platin and 5-fluorouracil, respectively. Diorganotin(IV) derivatives of mandelic acid are more cytotoxic than triorganotin analogues. Organotin(IV) derivatives of L-proline (except Bu3Sn(Pro) 16) are less cytotoxic than those of mandelic acid but their cytotoxicity is enhanced by complexion with 1,10-phenanthroline. This may be due to the structural planarity and extended π system of 1,10-phenanthroline which facilitates their transportation across the cell membrane and enhances the possibility of DNA intercalation over the planar L-proline ring, and eventually, their DNA binding affinity so as to interfere with the cellular functions of DNA leading to apoptosis. Various biophysical experiments such as DNA fragmentation, acridine orange and comet assays, and flow cytometry assay using annexin V–fluorescein isothiocyanate (FITC) and propidium iodide (PI) have been carried out in order to ascertain their mode of action. The observed results indicated that the major cause of cancer cell death is apoptosis, but a minor role played by necrosis cannot be excluded. It is concluded on the basis of the observed results that the nature and number of organic groups bonded to tin as well as the nature of counter anions play an important role in determining the cytotoxicity of organotin(IV) compounds.

A new family of D-2-hydroxyacid dehydrogenases that comprises D-mandelate dehydrogenases and 2-ketopantoate reductases

The gene for the D-mandelate dehydrogenase (DManDH) of Enterococcus faecalis IAM10071 was isolated by means of an activity staining procedure and PCR and expressed in Escherichia coli cells. The recombinant enzyme exhibited high catalytic activity toward various 2-ketoacid substrates with bulky hydrophobic side chains, particularly C3-branched substrates such as benzoylformate and 2-ketoisovalerate, and strict coenzyme specificity for NADH and NAD+. It showed marked sequence similarity with known NADP-dependent 2-ketopantoate reductases (KPR). These results indicate that together with KPR, D-ManDH constitutes a new family of D-2-hydroxyacid dehydrogenases that act on C3-branched 2-ketoacid substrates with various specificities for coenzymes and substrates.