MedKoo Cat#: 461420 | Name: Rosenonolactone

Description:

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

Rosenonolactone is a diterpenoid.

Chemical Structure

Rosenonolactone
Rosenonolactone
CAS#508-71-4

Theoretical Analysis

MedKoo Cat#: 461420

Name: Rosenonolactone

CAS#: 508-71-4

Chemical Formula: C20H28O3

Exact Mass: 316.2038

Molecular Weight: 316.44

Elemental Analysis: C, 75.91; H, 8.92; O, 15.17

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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Related CAS #
No Data
Synonym
Rosenonolactone;
IUPAC/Chemical Name
(1S,4aR,4bS,7S,8aS,10aR)-1,4b,7-trimethyl-7-vinyldodecahydro-9H-4a,1-(epoxymethano)phenanthrene-9,12-dione
InChi Key
HWECMADGHQKSLK-RJFGYBCDSA-N
InChi Code
InChI=1S/C20H28O3/c1-5-17(2)9-10-19(4)13(12-17)14(21)11-15-18(3)7-6-8-20(15,19)23-16(18)22/h5,13,15H,1,6-12H2,2-4H3/t13-,15-,17+,18+,19+,20-/m1/s1
SMILES Code
O=C1[C@@]2([H])C[C@@](C)(C=C)CC[C@]2(C)[C@@]34CCC[C@@](C(O4)=O)(C)[C@@]3([H])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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 316.44 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: Wang SR, Zhang L, Chen HP, Li ZH, Dong ZJ, Wei K, Liu JK. Four new spiroaxane sesquiterpenes and one new rosenonolactone derivative from cultures of Basidiomycete Trametes versicolor. Fitoterapia. 2015 Sep;105:127-31. doi: 10.1016/j.fitote.2015.06.017. Epub 2015 Jun 30. PubMed PMID: 26136058. 2: Kim YK, Son KH, Nam JY, Kim SU, Jeong TS, Lee WS, Bok SH, Kwon BM, Park YJ, Shin JM. Inhibition of cholesteryl ester transfer protein by rosenonolactone derivatives. J Antibiot (Tokyo). 1996 Aug;49(8):815-6. PubMed PMID: 8823516. 3: Hengstler JG, Löffler S, Schaefer M, Glatt HR, Fuchs J, Flesch P, Oesch F. DNA strand break induction, mutagenicity, and cytotoxicity of the mycotoxins 11-β-hydroxy-7-deoxy-rosenonolactone, rosenonolactone, and trichothecin. Mycotoxin Res. 1992 Sep;8(2):77-83. doi: 10.1007/BF03192220. PubMed PMID: 23606003. 4: Wang Y, Zhang L, Wang F, Li ZH, Dong ZJ, Liu JK. New Diterpenes from Cultures of the Fungus Engleromyces goetzii and Their CETP Inhibitory Activity. Nat Prod Bioprospect. 2015 Apr 8. [Epub ahead of print] PubMed PMID: 25850378; PubMed Central PMCID: PMC4402584. 5: Schabort JC, Roberts HA. Effect of versicolorin C, rosenonolactone and cyclopiazonic acid on bovine pancreas deoxyibonuclease. Biochem Pharmacol. 1971 Jan;20(1):243-6. PubMed PMID: 5106241. 6: Ellestad GA, Green B, Harris A, Whalley WB, Smith H. The chemistry of fungi. L. Rosenonolactone. J Chem Soc Perkin 1. 1965 Dec:7246-56. PubMed PMID: 5892025. 7: Schwenk S, Altmayer B, Eichhorn KW. Simultaneous detection of trichothecenes and rosenonolactone in grape juice and wine by capillary gas chromatography. J Chromatogr. 1988 Sep 16;448(3):424-7. PubMed PMID: 3243842. 8: Achilladelis B, Hanson JR. Studies in terpenoid biosynthesis. V. Biosynthesis of rosenonolactone. J Chem Soc Perkin 1. 1969;15:2010-4. PubMed PMID: 5387841. 9: Xu Y, Zhang HW, Yu CY, Lu Y, Chang Y, Zou ZM. Norcyperone, a novel skeleton norsesquiterpene from Cyperus rotundus L. Molecules. 2008 Oct 10;13(10):2474-81. doi: 10.3390/molecules13102474. PubMed PMID: 18923338. 10: Schäfer M, Hengstler J, Löffler S, Flesch P. Isolation, identification and toxicological characterization of TSS 1, a new mycotoxin of the rosenane class. Mycotoxin Res. 1990 Mar;6(1):21-30. doi: 10.1007/BF03192135. PubMed PMID: 23605359. 11: Zhang X, Li G, Ma J, Zeng Y, Ma W, Zhao P. Endophytic fungus Trichothecium roseum LZ93 antagonizing pathogenic fungi in vitro and its secondary metabolites. J Microbiol. 2010 Dec;48(6):784-90. doi: 10.1007/s12275-010-0173-z. Epub 2011 Jan 9. PubMed PMID: 21221935. 12: Loukaci A, Kayser O, Bindseil K, Siems K, Frevert J, Abreu PM. New trichothecenes isolated from Holarrhena floribunda. J Nat Prod. 2000 Jan;63(1):52-6. PubMed PMID: 10650079. 13: Schwenk S, Altmayer B, Eichhorn KW. [Significance of toxic metabolites of the fungus Trichothecium roseum Link ex Fr. for viticulture]. Z Lebensm Unters Forsch. 1989 Jun;188(6):527-30. German. PubMed PMID: 2763715. 14: Anis I, Ahmed S, Malik A, Yasin A, Choudary MI. Enzyme inhibitory constituents from Duranta repens. Chem Pharm Bull (Tokyo). 2002 Apr;50(4):515-8. PubMed PMID: 11964000.