Synonym
Dehydrogriseofulvin; Griseofulvin, dehydro-; Amudene; (-)-Dehydrogriseofulvin
IUPAC/Chemical Name
(S)-7-chloro-2',4,6-trimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohexane]-2',5'-diene-3,4'-dione
InChi Key
ISLYVROQSJYFAZ-KRWDZBQOSA-N
InChi Code
InChI=1S/C17H15ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h5-7H,1-4H3/t17-/m0/s1
SMILES Code
O=C1[C@]2(OC3=C(C(OC)=CC(OC)=C31)Cl)C(C)=CC(C=C2OC)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
350.75
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 |
1: Ribeiro AI, Costa ES, Thomasi SS, Brandão DFR, Vieira PC, Fernandes JB, Forim MR, Ferreira AG, Pascholati SF, Gusmão LFP, da Silva MFDGF. Biological and Chemical Control of Sclerotinia sclerotiorum using Stachybotrys levispora and Its Secondary Metabolite Griseofulvin. J Agric Food Chem. 2018 Jul 25;66(29):7627-7632. doi: 10.1021/acs.jafc.7b04197. Epub 2018 Jul 10. PMID: 29944364.
2: Ali T, Inagaki M, Chai HB, Wieboldt T, Rapplye C, Rakotondraibe LH. Halogenated Compounds from Directed Fermentation of Penicillium concentricum, an Endophytic Fungus of the Liverwort Trichocolea tomentella. J Nat Prod. 2017 May 26;80(5):1397-1403. doi: 10.1021/acs.jnatprod.6b01069. Epub 2017 Apr 14. PMID: 28409637.
3: Wubshet SG, Nyberg NT, Tejesvi MV, Pirttilä AM, Kajula M, Mattila S, Staerk D. Targeting high-performance liquid chromatography-high-resolution mass spectrometry-solid-phase extraction-nuclear magnetic resonance analysis with high-resolution radical scavenging profiles-Bioactive secondary metabolites from the endophytic fungus Penicillium namyslowskii. J Chromatogr A. 2013 Aug 9;1302:34-9. doi: 10.1016/j.chroma.2013.05.032. Epub 2013 May 22. PMID: 23827469.
4: Sato Y. [Biosynthesis and microbial transformation of griseofulvin and carcinogenesis and prevention of cancer by estrogens]. Yakugaku Zasshi. 1995 Nov;115(11):892-908. Japanese. doi: 10.1248/yakushi1947.115.11_892. PMID: 8568634.
5: Oda T, Hashimoto H, Sato Y. Regio- and stereoselective hydrogenation of 2'-demethoxy-2'-methyldehydrogriseofulvin, a symmetrical substrate, to (+)-2'-demethoxy-2'-methylgriseofulvin with a cell-free system of Streptomyces cinereocrocatus. Chem Pharm Bull (Tokyo). 1990 Feb;38(2):525-8. doi: 10.1248/cpb.38.525. PMID: 2337969.
6: Oda T, Sato Y. Stereochemistry of hydrogenation of (-)-dehydrogriseofulvin to (+)-griseofulvin with a cell-free system of Streptomyces cinereocrocatus. Chem Pharm Bull (Tokyo). 1985 Mar;33(3):1077-82. doi: 10.1248/cpb.33.1077. PMID: 4028292.
7: Segal A, Taylor EH. Conversion of griseophenone A to (+) or (-)-dehydrogriseofulvin in the presence of horseradish peroxidase and hydrogen peroxide. J Pharm Sci. 1968 May;57(5):874-6. doi: 10.1002/jps.2600570537. PMID: 5657554.
8: Isaka H, Okuda S, Tsuda K. [Transformation of griseophenone A to (+-)-dehydrogriseofulvin by Rhus laccase]. Yakugaku Zasshi. 1967 Oct;87(10):1288-9. Japanese. PMID: 4232312.
