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MedKoo Cat#: 145818 | Name: Unguinol

Description:

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

Unguinol is a biochemical compound derived from ergot alkaloids, specifically a product of Claviceps purpurea, a fungus that grows on rye. It is known to have antifungal and antimicrobial properties and has been studied for its potential therapeutic uses in dermatological treatments.

Chemical Structure

Unguinol
Unguinol
CAS#36587-59-4

Theoretical Analysis

MedKoo Cat#: 145818

Name: Unguinol

CAS#: 36587-59-4

Chemical Formula: C19H18O5

Exact Mass: 326.1200

Molecular Weight: 326.35

Elemental Analysis: C, 69.93; H, 5.56; O, 24.51

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Unguinol; Trisdechloronornidulin; Yasimin;
IUPAC/Chemical Name
(E)-6-(but-2-en-2-yl)-3,8-dihydroxy-1,9-dimethyl-11H-dibenzo[b,e][1,4]dioxepin-11-one
InChi Key
ZPPIKBUIYSSQEH-WEVVVXLNSA-N
InChi Code
1S/C19H18O5/c1-5-9(2)13-8-14(21)11(4)17-18(13)23-15-7-12(20)6-10(3)16(15)19(22)24-17/h5-8,20-21H,1-4H3/b9-5+
SMILES Code
C\C=C(/C)C1=C2OC3=CC(O)=CC(C)=C3C(=O)OC2=C(C)C(O)=C1
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 326.35 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: Morshed MT, Nguyen HT, Vuong D, Crombie A, Lacey E, Ogunniyi AD, Page SW, Trott DJ, Piggott AM. Semisynthesis and biological evaluation of a focused library of unguinol derivatives as next-generation antibiotics. Org Biomol Chem. 2021 Feb 7;19(5):1022-1036. doi: 10.1039/d0ob02460k. Epub 2021 Jan 14. PMID: 33443509. 2: Zwartsen A, Chottanapund S, Kittakoop P, Navasumrit P, Ruchirawat M, Van Duursen MBM, Van den Berg M. Evaluation of anti-tumour properties of two depsidones - Unguinol and Aspergillusidone D - in triple-negative MDA-MB-231 breast tumour cells. Toxicol Rep. 2019 Oct 20;6:1216-1222. doi: 10.1016/j.toxrep.2019.10.012. PMID: 31788435; PMCID: PMC6880138. 3: Domingos LTS, Martins RDS, Lima LM, Ghizelini AM, Ferreira-Pereira A, Cotinguiba F. Secondary Metabolites Diversity of Aspergillus unguis and Their Bioactivities: A Potential Target to Be Explored. Biomolecules. 2022 Dec 6;12(12):1820. doi: 10.3390/biom12121820. PMID: 36551248; PMCID: PMC9775040. 4: Motti CA, Bourne DG, Burnell JN, Doyle JR, Haines DS, Liptrot CH, Llewellyn LE, Ludke S, Muirhead A, Tapiolas DM. Screening marine fungi for inhibitors of the C4 plant enzyme pyruvate phosphate dikinase: unguinol as a potential novel herbicide candidate. Appl Environ Microbiol. 2007 Mar;73(6):1921-7. doi: 10.1128/AEM.02479-06. Epub 2007 Jan 12. PMID: 17220253; PMCID: PMC1828816. 5: Chantarasakha K, Yangchum A, Isaka M, Tepaamorndech S. Fungal Depsidones Stimulate AKT-Dependent Glucose Uptake in 3T3-L1 Adipocytes. J Nat Prod. 2024 Jul 26;87(7):1673-1681. doi: 10.1021/acs.jnatprod.3c01134. Epub 2024 Apr 10. PMID: 38597733; PMCID: PMC11287747. 6: Morshed MT, Vuong D, Crombie A, Lacey AE, Karuso P, Lacey E, Piggott AM. Expanding antibiotic chemical space around the nidulin pharmacophore. Org Biomol Chem. 2018 Apr 25;16(16):3038-3051. doi: 10.1039/c8ob00545a. PMID: 29634062. 7: Dos Santos EA, Marin VR, de Angelis DA, Ferreira H, Sass DC. Isolation and anti-Xanthomonas citri activity of unguinol produced by Aspergillus unguis CBMAI 2140. Lett Appl Microbiol. 2025 Feb 3:ovaf016. doi: 10.1093/lambio/ovaf016. Epub ahead of print. PMID: 39900472. 8: Nguyen HT, Morshed MT, Vuong D, Crombie A, Lacey E, Garg S, Pi H, Woolford L, Venter H, Page SW, Piggott AM, Trott DJ, Ogunniyi AD. Evaluation of Benzguinols as Next-Generation Antibiotics for the Treatment of Multidrug-Resistant Bacterial Infections. Antibiotics (Basel). 2021 Jun 16;10(6):727. doi: 10.3390/antibiotics10060727. PMID: 34208698; PMCID: PMC8233939. 9: Chottanapund S, Van Duursen MBM, Zwartsen A, Timtavorn S, Navasumrit P, Kittakoop P, Sureram S, Ruchirawat M, Van den Berg M. Depsidones inhibit aromatase activity and tumor cell proliferation in a co-culture of human primary breast adipose fibroblasts and T47D breast tumor cells. Toxicol Rep. 2017 Mar 19;4:165-171. doi: 10.1016/j.toxrep.2017.03.004. PMID: 28959637; PMCID: PMC5615129. 10: Handayani D, Aminah I, Pontana Putra P, Eka Putra A, Arbain D, Satriawan H, Efdi M, Celik I, Ekawati Tallei T. The depsidones from marine sponge-derived fungus Aspergillus unguis IB151 as an anti-MRSA agent: Molecular docking, pharmacokinetics analysis, and molecular dynamic simulation studies. Saudi Pharm J. 2023 Sep;31(9):101744. doi: 10.1016/j.jsps.2023.101744. Epub 2023 Aug 9. PMID: 37649676; PMCID: PMC10462890. 11: Yang WC, Bao HY, Liu YY, Nie YY, Yang JM, Hong PZ, Zhang Y. Depsidone Derivatives and a Cyclopeptide Produced by Marine Fungus Aspergillus unguis under Chemical Induction and by Its Plasma Induced Mutant. Molecules. 2018 Sep 3;23(9):2245. doi: 10.3390/molecules23092245. PMID: 30177651; PMCID: PMC6225302.

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