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MedKoo Cat#: 532418 | Name: 3-Chloro-4-hydroxyphenylacetic acid

Description:

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

3-Chloro-4-hydroxyphenylacetic acid is a bioactive chemical.

Chemical Structure

3-Chloro-4-hydroxyphenylacetic acid
3-Chloro-4-hydroxyphenylacetic acid
CAS#33697-81-3

Theoretical Analysis

MedKoo Cat#: 532418

Name: 3-Chloro-4-hydroxyphenylacetic acid

CAS#: 33697-81-3

Chemical Formula: C8H7ClO3

Exact Mass: 186.0084

Molecular Weight: 186.59

Elemental Analysis: C, 51.50; H, 3.78; Cl, 19.00; O, 25.72

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
3-Chloro-4-hydroxyphenylacetic acid
IUPAC/Chemical Name
3-Chloro-4-hydroxyphenylacetic acid
InChi Key
IYTUKSIOQKTZEG-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H7ClO3/c9-6-3-5(4-8(11)12)1-2-7(6)10/h1-3,10H,4H2,(H,11,12)
SMILES Code
O=C(O)CC1=CC=C(O)C(Cl)=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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 186.59 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
1: Kumar R, Sadowski MC, Levrier C, Nelson CC, Jones AJ, Holleran JP, Avery VM, Healy PC, Davis RA. Design and Synthesis of a Screening Library Using the Natural Product Scaffold 3-Chloro-4-hydroxyphenylacetic Acid. J Nat Prod. 2015 Apr 24;78(4):914-8. doi: 10.1021/np500856u. Epub 2015 Mar 24. PubMed PMID: 25803573. 2: Meng ZB, You XD, Suo D, Chen YL, Tang C, Yang JL, Zheng SJ. Root-derived auxin contributes to the phosphorus-deficiency-induced cluster-root formation in white lupin (Lupinus albus). Physiol Plant. 2013 Aug;148(4):481-9. doi: 10.1111/j.1399-3054.2012.01715.x. Epub 2012 Nov 20. PubMed PMID: 23067249. 3: Lanková M, Smith RS, Pesek B, Kubes M, Zazímalová E, Petrásek J, Hoyerová K. Auxin influx inhibitors 1-NOA, 2-NOA, and CHPAA interfere with membrane dynamics in tobacco cells. J Exp Bot. 2010 Aug;61(13):3589-98. doi: 10.1093/jxb/erq172. Epub 2010 Jul 1. PubMed PMID: 20595238; PubMed Central PMCID: PMC2921198. 4: Mani AR, Ippolito S, Moreno JC, Visser TJ, Moore KP. The metabolism and dechlorination of chlorotyrosine in vivo. J Biol Chem. 2007 Oct 5;282(40):29114-21. Epub 2007 Aug 8. PubMed PMID: 17686770. 5: Davis RA, Pierens GK, Parsons PG. Synthesis and spectroscopic characterisation of a combinatorial library based on the fungal natural product 3-chloro-4-hydroxyphenylacetamide. Magn Reson Chem. 2007 May;45(5):442-5. PubMed PMID: 17372964. 6: Kaneyasu T, Kobayashi A, Nakayama M, Fujii N, Takahashi H, Miyazawa Y. Auxin response, but not its polar transport, plays a role in hydrotropism of Arabidopsis roots. J Exp Bot. 2007;58(5):1143-50. Epub 2007 Jan 22. PubMed PMID: 17244629. 7: Joyce MG, Levy C, Gábor K, Pop SM, Biehl BD, Doukov TI, Ryter JM, Mazon H, Smidt H, van den Heuvel RH, Ragsdale SW, van der Oost J, Leys D. CprK crystal structures reveal mechanism for transcriptional control of halorespiration. J Biol Chem. 2006 Sep 22;281(38):28318-25. Epub 2006 Jun 27. PubMed PMID: 16803881. 8: Gábor K, Veríssimo CS, Cyran BC, Ter Horst P, Meijer NP, Smidt H, de Vos WM, van der Oost J. Characterization of CprK1, a CRP/FNR-type transcriptional regulator of halorespiration from Desulfitobacterium hafniense. J Bacteriol. 2006 Apr;188(7):2604-13. PubMed PMID: 16547048; PubMed Central PMCID: PMC1428393. 9: van de Pas BA, Jansen S, Dijkema C, Schraa G, de Vos WM, Stams AJ. Energy yield of respiration on chloroaromatic compounds in Desulfitobacterium dehalogenans. Appl Environ Microbiol. 2001 Sep;67(9):3958-63. PubMed PMID: 11525991; PubMed Central PMCID: PMC93115. 10: Parry G, Delbarre A, Marchant A, Swarup R, Napier R, Perrot-Rechenmann C, Bennett MJ. Novel auxin transport inhibitors phenocopy the auxin influx carrier mutation aux1. Plant J. 2001 Feb;25(4):399-406. PubMed PMID: 11260496. 11: Nguyen H, Finkelstein E, Reznick A, Cross C, van der Vliet A. Cigarette smoke impairs neutrophil respiratory burst activation by aldehyde-induced thiol modifications. Toxicology. 2001 Mar 7;160(1-3):207-17. PubMed PMID: 11246141. 12: Smidt H, van Leest M, van der Oost J, de Vos WM. Transcriptional regulation of the cpr gene cluster in ortho-chlorophenol-respiring Desulfitobacterium dehalogenans. J Bacteriol. 2000 Oct;182(20):5683-91. PubMed PMID: 11004165; PubMed Central PMCID: PMC94688. 13: Smidt H, Song D, van Der Oost J, de Vos WM. Random transposition by Tn916 in Desulfitobacterium dehalogenans allows for isolation and characterization of halorespiration-deficient mutants. J Bacteriol. 1999 Nov;181(22):6882-8. PubMed PMID: 10559152; PubMed Central PMCID: PMC94161. 14: Utkin I, Dalton DD, Wiegel J. Specificity of reductive dehalogenation of substituted ortho-chlorophenols by Desulfitobacterium dehalogenans JW/IU-DC1. Appl Environ Microbiol. 1995 Jan;61(1):346-51. Erratum in: Appl Environ Microbiol 1995 Apr;61(4):1677. PubMed PMID: 7887614; PubMed Central PMCID: PMC167288. 15: Markus A, Klages U, Lingens F. [Microbial degradation and 4-chlorophenylacetic acid. Chemical synthesis of 3-chloro-4-hydroxy-, 4-chloro-3-hydroxy- and 4-chloro-2-hydroxyphenylacetic acid (author's transl)]. Hoppe Seylers Z Physiol Chem. 1982 Apr;363(4):431-7. German. PubMed PMID: 7076135. 16: Klages U, Markus A, Lingens F. Degradation of 4-chlorophenylacetic acid by a Pseudomonas species. J Bacteriol. 1981 Apr;146(1):64-8. PubMed PMID: 7217006; PubMed Central PMCID: PMC217052.

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