Mandelic acid, (R)-
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MedKoo CAT#: 596493

CAS#: 611-71-2

Description: Mandelic acid, (R)- is an aromatic alpha hydroxy acid. It is a white crystalline solid that is soluble in water and polar organic solvents. It is a useful precursor to various drugs. The molecule is chiral. The racemic mixture is known as paramandelic acid.


Chemical Structure

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Mandelic acid, (R)-
CAS# 611-71-2

Theoretical Analysis

MedKoo Cat#: 596493
Name: Mandelic acid, (R)-
CAS#: 611-71-2
Chemical Formula: C8H8O3
Exact Mass: 152.0473
Molecular Weight: 152.14
Elemental Analysis: C, 63.15; H, 5.30; O, 31.55

Price and Availability

Size Price Availability Quantity
5.0g USD 205.0 2 Weeks
25.0g USD 360.0 2 Weeks
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Synonym: Mandelic acid, (R)-; Mandelic acid, D-; D-2-Phenylglycolic acid;

IUPAC/Chemical Name: (R)-2-hydroxy-2-phenylacetic acid

InChi Key: IWYDHOAUDWTVEP-SSDOTTSWSA-N

InChi Code: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1

SMILES Code: O=C(O)[C@H](O)C1=CC=CC=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 152.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Deng X, Li W, Ding G, Chen X. Enantioselective separation of RS-mandelic acid using β-cyclodextrin modified Fe(3)O(4)@SiO(2)/Au microspheres. Analyst. 2018 May 29;143(11):2665-2673. doi: 10.1039/c8an00427g. PubMed PMID: 29761177.

2: Deshmukh DG, Bangal MN, Patekar MR, Medhane VJ, Mathad VT. Investigation of Mechanistic Pathway for Trimethyl Borate Mediated Amidation of (R)-Mandelic Acid for the Synthesis of Mirabegron, an Antimuscarinic Agent. Acta Chim Slov. 2018 Mar;65(1):239-245. PubMed PMID: 29562093.

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4: Duffin RN, Blair VL, Kedzierski L, Andrews PC. Comparative stability, toxicity and anti-leishmanial activity of triphenyl antimony(v) and bismuth(v) α-hydroxy carboxylato complexes. Dalton Trans. 2018 Jan 15;47(3):971-980. doi: 10.1039/c7dt04171c. PubMed PMID: 29260831.

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7: Zhang XH, Liu ZQ, Xue YP, Wang YS, Yang B, Zheng YG. Production of R-Mandelic Acid Using Nitrilase from Recombinant E. coli Cells Immobilized with Tris(Hydroxymethyl)Phosphine. Appl Biochem Biotechnol. 2018 Mar;184(3):1024-1035. doi: 10.1007/s12010-017-2604-3. Epub 2017 Sep 22. PubMed PMID: 28936681.

8: Soleimani E, Bahrami A, Afkhami A, Shahna FG. Selective determination of mandelic acid in urine using molecularly imprinted polymer in microextraction by packed sorbent. Arch Toxicol. 2018 Jan;92(1):213-222. doi: 10.1007/s00204-017-2057-z. Epub 2017 Sep 4. Erratum in: Arch Toxicol. 2018 Jan 8;:. PubMed PMID: 28871328.

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11: Bearne SL, St Maurice M. A Paradigm for CH Bond Cleavage: Structural and Functional Aspects of Transition State Stabilization by Mandelate Racemase. Adv Protein Chem Struct Biol. 2017;109:113-160. doi: 10.1016/bs.apcsb.2017.04.007. Epub 2017 Jun 9. Review. PubMed PMID: 28683916.

12: Borazjani M, Mehdinia A, Jabbari A. Betamethasone-based chiral electrochemical sensor coupled to chemometric methods for determination of mandelic acid enantiomers. J Mol Recognit. 2017 Dec;30(12). doi: 10.1002/jmr.2653. Epub 2017 Jul 4. PubMed PMID: 28675615.

13: Flieger J, Feder-Kubis J, Tatarczak-Michalewska M, Płazińska A, Madejska A, Swatko-Ossor M. Natural terpene derivatives as new structural task-specific ionic liquids to enhance the enantiorecognition of acidic enantiomers on teicoplanin-based stationary phase by high-performance liquid chromatography. J Sep Sci. 2017 Jun;40(11):2374-2381. doi: 10.1002/jssc.201700197. Epub 2017 May 8. PubMed PMID: 28426156.

14: Chen X, Yang C, Wang P, Zhang X, Bao B, Li D, Shi R. Stereoselective biotransformation of racemic mandelic acid using immobilized laccase and (S)-mandelate dehydrogenase. Bioresour Bioprocess. 2017;4(1):2. doi: 10.1186/s40643-016-0135-3. Epub 2017 Jan 3. PubMed PMID: 28133593; PubMed Central PMCID: PMC5236080.

15: Vitali L, Gonçalves S, Rodrigues V, Fávere VT, Micke GA. Development of a fast method for simultaneous determination of hippuric acid, mandelic acid, and creatinine in urine by capillary zone electrophoresis using polymer multilayer-coated capillary. Anal Bioanal Chem. 2017 Mar;409(7):1943-1950. doi: 10.1007/s00216-016-0142-4. Epub 2016 Dec 17. PubMed PMID: 27988799.

16: Revu O, Prasad KR. Total Synthesis of the Bis-silyl Ether of (+)-15-epi-Aetheramide A. J Org Chem. 2017 Jan 6;82(1):438-460. doi: 10.1021/acs.joc.6b02535. Epub 2016 Dec 12. PubMed PMID: 27936701.

17: Sun Y, Mei Y, Quan J, Xiao X, Zhang L, Tian D, Li H. The macroscopic wettable surface: fabricated by calix[4]arene-based host-guest interaction and chiral discrimination of glucose. Chem Commun (Camb). 2016 Dec 13;52(100):14416-14418. Erratum in: Chem Commun (Camb). 2017 Jan 16;53(5):984. PubMed PMID: 27901133.

18: Bruce S, Roberts W, Teller C, Colvan L. The Effects of a Daily Skincare Regimen on Maintaining the Benefits Obtained from Previous Chemical Resurfacing Treatments. J Drugs Dermatol. 2016 Sep 1;15(9):1145-50. PubMed PMID: 27602981.

19: Yutthalekha T, Wattanakit C, Lapeyre V, Nokbin S, Warakulwit C, Limtrakul J, Kuhn A. Asymmetric synthesis using chiral-encoded metal. Nat Commun. 2016 Aug 26;7:12678. doi: 10.1038/ncomms12678. PubMed PMID: 27562028; PubMed Central PMCID: PMC5007459.

20: Yang C, Ye L, Gu J, Yang X, Li A, Yu H. Directed evolution of mandelate racemase by a novel high-throughput screening method. Appl Microbiol Biotechnol. 2017 Feb;101(3):1063-1072. doi: 10.1007/s00253-016-7790-3. Epub 2016 Aug 24. PubMed PMID: 27557723.