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MedKoo Cat#: 581004 | Name: Hymecromone
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Description:

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

Hymecromone (4-methylumbelliferone) is a coumarin derivative that functions as a selective inhibitor of hyaluronan (HA) synthesis by depleting intracellular UDP-glucuronic acid. It is widely used in research to study extracellular matrix remodeling, tumor progression, and inflammation due to its ability to modulate HA-dependent signaling pathways. Hymecromone also exhibits choleretic and antispasmodic properties, making it a useful tool in both biochemical assays and preclinical models of liver and biliary diseases.

Chemical Structure

Hymecromone
Hymecromone
CAS#90-33-5

Theoretical Analysis

MedKoo Cat#: 581004

Name: Hymecromone

CAS#: 90-33-5

Chemical Formula: C10H8O3

Exact Mass: 176.0473

Molecular Weight: 176.17

Elemental Analysis: C, 68.18; H, 4.58; O, 27.24

Price and Availability

Size Price Availability Quantity
25g USD 350.00 2 Weeks
100g USD 500.00 2 Weeks
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Related CAS #
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Synonym
Hymecromone; 4-MU; 4-Methylumbelliferone; Imecromone;
IUPAC/Chemical Name
7-Hydroxy-4-methyl-2H-chromen-2-one
InChi Key
HSHNITRMYYLLCV-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
SMILES Code
O=C1C=C(C)C2=C(O1)C=C(O)C=C2
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

Preparing Stock Solutions

The following data is based on the product molecular weight 176.17 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: Zhu H, Ma X, Kong JY, Zhang M, Kenttämaa HI. Identification of Carboxylate, Phosphate, and Phenoxide Functionalities in Deprotonated Molecules Related to Drug Metabolites via Ion-Molecule Reactions with water and Diethylhydroxyborane. J Am Soc Mass Spectrom. 2017 Jul 24. doi: 10.1007/s13361-017-1713-0. [Epub ahead of print] PubMed PMID: 28741125. 2: Grignon C, Dupuis A, Albouy-Llaty M, Condylis M, Barrier L, Carato P, Brunet B, Migeot V, Venisse N. Validation of a probe for assessing deconjugation of glucuronide and sulfate phase II metabolites assayed through LC-MS/MS in biological matrices. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Sep 1;1061-1062:72-78. doi: 10.1016/j.jchromb.2017.07.013. Epub 2017 Jul 10. PubMed PMID: 28710970. 3: Kudo D, Suto A, Hakamada K. The Development of a Novel Therapeutic Strategy to Target Hyaluronan in the Extracellular Matrix of Pancreatic Ductal Adenocarcinoma. Int J Mol Sci. 2017 Mar 9;18(3). pii: E600. doi: 10.3390/ijms18030600. Review. PubMed PMID: 28282922; PubMed Central PMCID: PMC5372616. 4: Ouyang X, Panetta NJ, Talbott MD, Payumo AY, Halluin C, Longaker MT, Chen JK. Hyaluronic acid synthesis is required for zebrafish tail fin regeneration. PLoS One. 2017 Feb 16;12(2):e0171898. doi: 10.1371/journal.pone.0171898. eCollection 2017. PubMed PMID: 28207787; PubMed Central PMCID: PMC5313160. 5: Shinomiya K, Zaima K, Harada Y, Yasue M, Harikai N, Tokura K, Ito Y. Comparison of the peak resolution and the stationary phase retention between the satellite and the planetary motions using the coil satellite centrifuge with counter-current chromatographic separation of 4-methylumbelliferyl sugar derivatives. J Chromatogr A. 2017 Jan 20;1481:64-72. doi: 10.1016/j.chroma.2016.12.027. Epub 2016 Dec 21. PubMed PMID: 28040269; PubMed Central PMCID: PMC5222749. 6: Liu D, Wu J, Xie H, Liu M, Takau I, Zhang H, Xiong Y, Xia C. Inhibitory Effect of Hesperetin and Naringenin on Human UDP-Glucuronosyltransferase Enzymes: Implications for Herb-Drug Interactions. Biol Pharm Bull. 2016;39(12):2052-2059. PubMed PMID: 27904048. 7: Ikuta K, Ota T, Zhuo L, Urakawa H, Kozawa E, Hamada S, Kimata K, Ishiguro N, Nishida Y. Antitumor effects of 4-methylumbelliferone, a hyaluronan synthesis inhibitor, on malignant peripheral nerve sheath tumor. Int J Cancer. 2017 Jan 15;140(2):469-479. doi: 10.1002/ijc.30460. Epub 2016 Oct 18. PubMed PMID: 27706810. 8: Li X, Zeng H, Wang P, Lin L, Liu L, Zhen P, Fu Y, Lu P, Zhu H. Reactivation of latent HIV-1 in latently infected cells by coumarin compounds: Hymecromone and ScoparoneReactivation of Latent HIV-1 in Latently Infected Cells by Coumarin Compounds: Hymecromone and Scoparone. Curr HIV Res. 2016;14(6):484-490. PubMed PMID: 27697031. 9: Huang RZ, Hua SX, Wang CY, Pan YM, Qin JM, Ding ZY, Zhang Y, Wang HS. 4-Methylumbelliferones Analogues as Anticancer Agents: Synthesis and in Cell Pharmacological Studies. Anticancer Agents Med Chem. 2017;17(4):576-589. doi: 10.2174/1871520616666160926113109. PubMed PMID: 27671299. 10: Xie H, Wu J, Liu D, Liu M, Zhang H, Huang S, Xiong Y, Xia C. In vitro inhibition of UGT1A3, UGT1A4 by ursolic acid and oleanolic acid and drug-drug interaction risk prediction. Xenobiotica. 2017 Sep;47(9):785-792. doi: 10.1080/00498254.2016.1234087. Epub 2016 Sep 22. PubMed PMID: 27600106. 11: Liu X, Cao YF, Dong PP, Zhu LL, Zhao Z, Wu X, Fu ZW, Huang CT, Fang ZZ, Sun HZ. The inhibition of UDP-glucuronosyltransferases (UGTs) by vitamin A. Xenobiotica. 2017 May;47(5):376-381. doi: 10.1080/00498254.2016.1198841. Epub 2016 Jun 30. PubMed PMID: 27359323. 12: Al-Majedy YK, Al-Amiery AA, Kadhum AA, Mohamad AB. Antioxidant Activities of 4-Methylumbelliferone Derivatives. PLoS One. 2016 May 31;11(5):e0156625. doi: 10.1371/journal.pone.0156625. eCollection 2016. PubMed PMID: 27243231; PubMed Central PMCID: PMC4887010. 13: Kuipers HF, Nagy N, Ruppert SM, Sunkari VG, Marshall PL, Gebe JA, Ishak HD, Keswani SG, Bollyky J, Frymoyer AR, Wight TN, Steinman L, Bollyky PL. The pharmacokinetics and dosing of oral 4-methylumbelliferone for inhibition of hyaluronan synthesis in mice. Clin Exp Immunol. 2016 Sep;185(3):372-81. doi: 10.1111/cei.12815. PubMed PMID: 27218304; PubMed Central PMCID: PMC4991518. 14: Ishizuka S, Askew EB, Ishizuka N, Knudson CB, Knudson W. 4-Methylumbelliferone Diminishes Catabolically Activated Articular Chondrocytes and Cartilage Explants via a Mechanism Independent of Hyaluronan Inhibition. J Biol Chem. 2016 Jun 3;291(23):12087-104. doi: 10.1074/jbc.M115.709683. Epub 2016 Apr 25. PubMed PMID: 27129266; PubMed Central PMCID: PMC4933260. 15: Lv X, Wang XX, Hou J, Fang ZZ, Wu JJ, Cao YF, Liu SW, Ge GB, Yang L. Comparison of the inhibitory effects of tolcapone and entacapone against human UDP-glucuronosyltransferases. Toxicol Appl Pharmacol. 2016 Jun 15;301:42-9. doi: 10.1016/j.taap.2016.04.009. Epub 2016 Apr 16. PubMed PMID: 27089846. 16: Zayane M, Rahmouni A, Daami-Remadi M, Ben Mansour M, Romdhane A, Ben Jannet H. Design and synthesis of antimicrobial, anticoagulant, and anticholinesterase hybrid molecules from 4-methylumbelliferone. J Enzyme Inhib Med Chem. 2016 Dec;31(6):1566-75. doi: 10.3109/14756366.2016.1158171. Epub 2016 Apr 1. PubMed PMID: 27033638. 17: Olivares CN, Alaniz LD, Menger MD, Barañao RI, Laschke MW, Meresman GF. Inhibition of Hyaluronic Acid Synthesis Suppresses Angiogenesis in Developing Endometriotic Lesions. PLoS One. 2016 Mar 28;11(3):e0152302. doi: 10.1371/journal.pone.0152302. eCollection 2016. PubMed PMID: 27018976; PubMed Central PMCID: PMC4809563. 18: Kato N, Shibata K, Uchigasaki S, Kurose A. Relation between hyaluronan synthesis and cell morphology in ovarian clear cell carcinomas. Pathol Int. 2016 Apr;66(4):218-23. doi: 10.1111/pin.12405. Epub 2016 Mar 27. PubMed PMID: 27017153. 19: Xiao W, Lu MH. Comparison of the inhibition capability of oleanolic acid and betulinic acid towards drug-metabolizing enzymes. Afr Health Sci. 2015 Sep;15(3):1011-5. doi: 10.4314/ahs.v15i3.40. PubMed PMID: 26957994; PubMed Central PMCID: PMC4765439. 20: Irani S, Yogesha SD, Mayfield J, Zhang M, Zhang Y, Matthews WL, Nie G, Prescott NA, Zhang YJ. Structure of Saccharomyces cerevisiae Rtr1 reveals an active site for an atypical phosphatase. Sci Signal. 2016 Mar 1;9(417):ra24. doi: 10.1126/scisignal.aad4805. PubMed PMID: 26933063; PubMed Central PMCID: PMC4801511.

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