Mandelic acid, (R)- | CAS#611-71-2 | aromatic alpha hydroxy acid

Mandelic acid, (R)-
featured

WARNING: This product is for research use only, not for human or veterinary use.

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

Mandelic acid, (R)-

CAS# 611-71-2

Instruction

Theoretical Analysis

MedKoo Cat#: 596493
Name: Mandelic acid, (R)-
CAS#: 611-71-2
Chemical Formula: C8H8O3
Exact Mass: 152.05
Molecular Weight: 152.140
Elemental Analysis: C, 63.15; H, 5.30; O, 31.55

Price and Availability

Size	Price	Availability
25g	USD 250	2 weeks
100g	USD 450	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: (R)-(-)-Mandelic acid; D-Mandelic acid; D-α-Hydroxyphenylacetic 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

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

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.

3: Martínková L, Křen V. Biocatalytic production of mandelic acid and analogues: a review and comparison with chemical processes. Appl Microbiol Biotechnol. 2018 May;102(9):3893-3900. doi: 10.1007/s00253-018-8894-8. Epub 2018 Mar 10. Review. PubMed PMID: 29525852.

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.

5: Hajizadeh Y, Teiri H, Nazmara S, Parseh I. Environmental and biological monitoring of exposures to VOCs in a petrochemical complex in Iran. Environ Sci Pollut Res Int. 2018 Mar;25(7):6656-6667. doi: 10.1007/s11356-017-1045-4. Epub 2017 Dec 19. PubMed PMID: 29260472.

6: Wu LL, Liang RP, Chen J, Qiu JD. Separation of chiral compounds using magnetic molecularly imprinted polymer nanoparticles as stationary phase by microchip capillary electrochromatography. Electrophoresis. 2018 Jan;39(2):356-362. doi: 10.1002/elps.201700334. Epub 2017 Nov 9. PubMed PMID: 29067704.

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.

9: Lu R, He Q, Feng C, Peng Y. Enantioselective resolution of 4-chloromandelic acid by liquid-liquid extraction using 2-chloro-N-carbobenzyloxy-L-amino acid. Chirality. 2017 Nov;29(11):708-715. doi: 10.1002/chir.22738. Epub 2017 Aug 23. PubMed PMID: 28833485.

10: Wong LWY, Kan JWH, Sung HHY, Williams ID. Chiral bis(mandelato)borate salts for resolution via metathesis crystallization. Acta Crystallogr C Struct Chem. 2017 Aug 1;73(Pt 8):625-631. doi: 10.1107/S2053229617009718. Epub 2017 Jul 21. PubMed PMID: 28776514.

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.

Your view history

Mandelic acid, (R)- featured