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

Hodoodo CAT#: H591714

CAS#: 644-78-0

Description: 2-Hydroxychalcone can be used as antiparasitic hit compounds when Methoxylated.

Chemical Structure

2-Hydroxychalcone

CAS# 644-78-0

Instruction

Theoretical Analysis

Hodoodo Cat#: H591714
Name: 2-Hydroxychalcone
CAS#: 644-78-0
Chemical Formula: C15H12O2
Exact Mass: 224.08
Molecular Weight: 224.260
Elemental Analysis: C, 80.34; H, 5.39; O, 14.27

Price and Availability

Size	Price	Availability
5g	USD 230	2 Weeks
25g	USD 440	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. Hodoodo 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: 2-Hydroxychalcone; AI3-00855; AI3 00855; AI300855

IUPAC/Chemical Name: 2-Hydroxychalcone

InChi Key: UDOOPSJCRMKSGL-ZHACJKMWSA-N

InChi Code: InChI=1S/C15H12O2/c16-14-9-5-4-8-13(14)10-11-15(17)12-6-2-1-3-7-12/h1-11,16H/b11-10+

SMILES Code: O=C(C1=CC=CC=C1)/C=C/C2=CC=CC=C2O

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 224.26 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:

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1: Żyszka-Haberecht B, Poliwoda A, Lipok J. Biocatalytic hydrogenation of the C=C bond in the enone unit of hydroxylated chalcones-process arising from cyanobacterial adaptations. Appl Microbiol Biotechnol. 2018 Jun 4. doi: 10.1007/s00253-018-9109-z. [Epub ahead of print] PubMed PMID: 29869071.

2: Serdiuk IE, Wera M, Roshal AD. Structural and Spectral Features of 4'-Substituted 2'-Hydroxychalcones in Solutions and Crystals: Spectroscopic and Theoretical Investigations. J Phys Chem A. 2018 Mar 1;122(8):2030-2038. doi: 10.1021/acs.jpca.7b10361. Epub 2018 Feb 15. PubMed PMID: 29401395.

3: Dommett M, Rivera M, Crespo-Otero R. How Inter- and Intramolecular Processes Dictate Aggregation-Induced Emission in Crystals Undergoing Excited-State Proton Transfer. J Phys Chem Lett. 2017 Dec 21;8(24):6148-6153. doi: 10.1021/acs.jpclett.7b02893. Epub 2017 Dec 11. PubMed PMID: 29219318.

4: Zahid NI, Mahmood MS, Subramanian B, Mohd Said S, Abou-Zied OK. New Insight into the Origin of the Red/Near-Infrared Intense Fluorescence of a Crystalline 2-Hydroxychalcone Derivative: A Comprehensive Picture from the Excited-State Femtosecond Dynamics. J Phys Chem Lett. 2017 Nov 16;8(22):5603-5608. doi: 10.1021/acs.jpclett.7b02601. Epub 2017 Nov 3. PubMed PMID: 29094952.

5: Borsari C, Santarem N, Torrado J, Olías AI, Corral MJ, Baptista C, Gul S, Wolf M, Kuzikov M, Ellinger B, Witt G, Gribbon P, Reinshagen J, Linciano P, Tait A, Costantino L, Freitas-Junior LH, Moraes CB, Bruno Dos Santos P, Alcântara LM, Franco CH, Bertolacini CD, Fontana V, Tejera Nevado P, Clos J, Alunda JM, Cordeiro-da-Silva A, Ferrari S, Costi MP. Methoxylated 2'-hydroxychalcones as antiparasitic hit compounds. Eur J Med Chem. 2017 Jan 27;126:1129-1135. doi: 10.1016/j.ejmech.2016.12.017. Epub 2016 Dec 9. PubMed PMID: 28064141.

6: Dommett M, Crespo-Otero R. Excited state proton transfer in 2'-hydroxychalcone derivatives. Phys Chem Chem Phys. 2017 Jan 18;19(3):2409-2416. doi: 10.1039/c6cp07541j. PubMed PMID: 28058421.

7: Křikavová R, Vančo J, Trávníček Z, Hutyra J, Dvořák Z. Design and characterization of highly in vitro antitumor active ternary copper(II) complexes containing 2'-hydroxychalcone ligands. J Inorg Biochem. 2016 Oct;163:8-17. doi: 10.1016/j.jinorgbio.2016.07.005. Epub 2016 Jul 9. PubMed PMID: 27423037.

8: Iovine V, Benni I, Sabia R, D'Acquarica I, Fabrizi G, Botta B, Calcaterra A. Total Synthesis of (±)-Kuwanol E. J Nat Prod. 2016 Oct 28;79(10):2495-2503. Epub 2016 Sep 22. PubMed PMID: 27656763.

9: Sukumaran SD, Chee CF, Viswanathan G, Buckle MJ, Othman R, Abd Rahman N, Chung LY. Synthesis, Biological Evaluation and Molecular Modelling of 2'-Hydroxychalcones as Acetylcholinesterase Inhibitors. Molecules. 2016 Jul 22;21(7). pii: E955. doi: 10.3390/molecules21070955. PubMed PMID: 27455222.

10: Stompor M, Kałużny M, Żarowska B. Biotechnological methods for chalcone reduction using whole cells of Lactobacillus, Rhodococcus and Rhodotorula strains as a way to produce new derivatives. Appl Microbiol Biotechnol. 2016 Oct;100(19):8371-84. doi: 10.1007/s00253-016-7607-4. Epub 2016 May 21. PubMed PMID: 27209040.

11: Lahyani A, Trabelsi M. Ultrasonic-assisted synthesis of flavones by oxidative cyclization of 2'-hydroxychalcones using iodine monochloride. Ultrason Sonochem. 2016 Jul;31:626-30. doi: 10.1016/j.ultsonch.2016.02.018. Epub 2016 Feb 11. PubMed PMID: 26964989.

12: Raghav N, Garg S, Ravish I. Conversion of 2'-substituted chalcones in the presence of BSA as evidenced by ¹H NMR studies. Int J Biol Macromol. 2016 Apr;85:23-8. doi: 10.1016/j.ijbiomac.2015.12.060. Epub 2015 Dec 23. PubMed PMID: 26723247.

13: Li X, Han J, Jones AX, Lei X. Chiral Boron Complex-Promoted Asymmetric Diels-Alder Cycloaddition and Its Application in Natural Product Synthesis. J Org Chem. 2016 Jan 15;81(2):458-68. doi: 10.1021/acs.joc.5b02248. Epub 2015 Dec 22. PubMed PMID: 26693852.

14: Kaufmann KB, Al-Rifai N, Ulbrich F, Schallner N, Rücker H, Enzinger M, Petkes H, Pitzl S, Goebel U, Amslinger S. The Cytoprotective Effects of E-α-(4-Methoxyphenyl)-2',3,4,4'-Tetramethoxychalcone (E-α-p-OMe-C6H4-TMC)--A Novel and Non-Cytotoxic HO-1 Inducer. PLoS One. 2015 Nov 13;10(11):e0142932. doi: 10.1371/journal.pone.0142932. eCollection 2015. PubMed PMID: 26565402; PubMed Central PMCID: PMC4643879.

15: Li Y, Li K, He J. A 'turn-on' fluorescent chemosensor for quantification of serum albumin in aqueous solution at neutral pH. Luminescence. 2016 May;31(3):905-10. doi: 10.1002/bio.3052. Epub 2015 Nov 10. PubMed PMID: 26553312.

16: Kim H, Youn GS, An SY, Kwon HY, Choi SY, Park J. 2,3-Dimethoxy-2'-hydroxychalcone ameliorates TNF-α-induced ICAM-1 expression and subsequent monocyte adhesiveness via NF-kappaB inhibition and HO-1 induction in HaCaT cells. BMB Rep. 2016 Jan;49(1):57-62. doi: 10.5483/BMBRep.2016.49.1.141. PubMed PMID: 26277982; PubMed Central PMCID: PMC4914214.

17: Cheng X, Wang K, Huang S, Zhang H, Zhang H, Wang Y. Organic Crystals with Near-Infrared Amplified Spontaneous Emissions Based on 2'-Hydroxychalcone Derivatives: Subtle Structure Modification but Great Property Change. Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8369-73. doi: 10.1002/anie.201503914. Epub 2015 Jun 3. PubMed PMID: 26036645.

18: Simmler C, Jones T, Anderson JR, Nikolić DC, van Breemen RB, Soejarto DD, Chen SN, Pauli GF. Species-specific Standardisation of Licorice by Metabolomic Profiling of Flavanones and Chalcones. Phytochem Anal. 2014 Jul-Aug;25(4):378-88. doi: 10.1002/pca.2472. Epub 2013 Nov 13. PubMed PMID: 25859589; PubMed Central PMCID: PMC4391967.

19: Kupcewicz B, Jarzęcki AA, Małecka M, Krajewska U, Rozalski M. Cytotoxic activity of substituted chalcones in terms of molecular electronic properties. Bioorg Med Chem Lett. 2014 Sep 1;24(17):4260-5. doi: 10.1016/j.bmcl.2014.07.027. Epub 2014 Jul 22. PubMed PMID: 25091929.

20: Raghav N, Garg S. SAR studies of o-hydroxychalcones and their cyclized analogs and study them as novel inhibitors of cathepsin B and cathepsin H. Eur J Pharm Sci. 2014 Aug 18;60:55-63. doi: 10.1016/j.ejps.2014.04.006. Epub 2014 Apr 26. PubMed PMID: 24780403.

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