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MedKoo Cat#: 581712 | Name: Drimane

Description:

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

Drimane is a bicyclic sesquiterpene. It is the parent structure of many natural products with various biological activity.

Chemical Structure

Drimane
Drimane
CAS#5951-58-6

Theoretical Analysis

MedKoo Cat#: 581712

Name: Drimane

CAS#: 5951-58-6

Chemical Formula: C15H28

Exact Mass: 208.2191

Molecular Weight: 208.39

Elemental Analysis: C, 86.46; H, 13.54

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
Drimane; Decahydro-1,2,5,5,8a-pentamethylnaphthalene stereoisomer.
IUPAC/Chemical Name
1,1,4a,5,6-pentamethyldecahydronaphthalene
InChi Key
CVRSZZJUWRLRDE-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H28/c1-11-7-8-13-14(3,4)9-6-10-15(13,5)12(11)2/h11-13H,6-10H2,1-5H3
SMILES Code
CC1CCC2C(CCCC2(C1C)C)(C)C
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 208.39 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
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Epub 2018 Oct 5. PubMed PMID: 30320372; PubMed Central PMCID: PMC6203145. 4: Ma M, Feng J, Wang D, Chen SW, Xu H. Synthesis and Antifungal Activities of Drimane-Amide Derivatives from Sclareol. Comb Chem High Throughput Screen. 2018;21(7):501-509. doi: 10.2174/1386207321666180925164358. PubMed PMID: 30255746. 5: Montenegro I, Madrid A, Cuellar M, Seeger M, Alfaro JF, Besoain X, Martínez JP, Ramirez I, Olguín Y, Valenzuela M. Biopesticide Activity from Drimanic Compounds to Control Tomato Pathogens. Molecules. 2018 Aug 16;23(8). pii: E2053. doi: 10.3390/molecules23082053. PubMed PMID: 30115841; PubMed Central PMCID: PMC6222531. 6: Nyaba ZN, Murambiwa P, Opoku AR, Mukaratirwa S, Shode FO, Simelane MBC. Isolation, characterization, and biological evaluation of a potent anti-malarial drimane sesquiterpene from Warburgia salutaris stem bark. Malar J. 2018 Aug 15;17(1):296. doi: 10.1186/s12936-018-2439-6. PubMed PMID: 30111328; PubMed Central PMCID: PMC6094573. 7: Lai Y, Zhang N, Zhang Y, Chen JH, Yang Z. Asymmetric Total Syntheses of Insulicolide A, 14- O-Acetylinsulicolide A, 6β,9α-Dihydroxy-14- p-nitrobenzoylcinnamolide, and 7α,14-Dihydroxy-6β- p-nitrobenzoylconfertifolin. Org Lett. 2018 Jul 20;20(14):4298-4301. doi: 10.1021/acs.orglett.8b01733. Epub 2018 Jun 29. PubMed PMID: 29957964. 8: Kwon J, Lee H, Seo YH, Yun J, Lee J, Kwon HC, Guo Y, Kang JS, Kim JJ, Lee D. Cytotoxic Drimane Sesquiterpenoids Isolated from Perenniporia maackiae. J Nat Prod. 2018 Jun 22;81(6):1444-1450. doi: 10.1021/acs.jnatprod.8b00175. Epub 2018 Jun 7. PubMed PMID: 29878761. 9: Fratoni E, de Athayde AE, da Silva Machado M, Zermiani T, Venturi I, Corrêa Dos Santos M, Lobato F, Cechinel Filho V, Franchi GC Jr, Nowill AE, Santin JR, Malheiros A. Antiproliferative and toxicological properties of drimanes obtained from Drimys brasiliensis stem barks. Biomed Pharmacother. 2018 Jul;103:1498-1506. doi: 10.1016/j.biopha.2018.04.103. Epub 2018 May 7. PubMed PMID: 29864935. 10: Arias HR, Feuerbach D, Schmidt B, Heydenreich M, Paz C, Ortells MO. Drimane Sesquiterpenoids Noncompetitively Inhibit Human α4β2 Nicotinic Acetylcholine Receptors with Higher Potency Compared to Human α3β4 and α7 Subtypes. J Nat Prod. 2018 Apr 27;81(4):811-817. doi: 10.1021/acs.jnatprod.7b00893. Epub 2018 Apr 10. PubMed PMID: 29634269. 11: Inocente EA, Shaya M, Acosta N, Rakotondraibe LH, Piermarini PM. A natural agonist of mosquito TRPA1 from the medicinal plant Cinnamosma fragrans that is toxic, antifeedant, and repellent to the yellow fever mosquito Aedes aegypti. PLoS Negl Trop Dis. 2018 Feb 9;12(2):e0006265. doi: 10.1371/journal.pntd.0006265. eCollection 2018 Feb. PubMed PMID: 29425195; PubMed Central PMCID: PMC5823474. 12: Karmahapatra S, Kientz C, Shetty S, Yalowich JC, Rakotondraibe LH. Capsicodendrin from Cinnamosma fragrans Exhibits Antiproliferative and Cytotoxic Activity in Human Leukemia Cells: Modulation by Glutathione. J Nat Prod. 2018 Mar 23;81(3):625-629. doi: 10.1021/acs.jnatprod.7b00887. Epub 2018 Feb 6. PubMed PMID: 29406734. 13: Montenegro IJ, Del Corral S, Diaz Napal GN, Carpinella MC, Mellado M, Madrid AM, Villena J, Palacios SM, Cuellar MA. Antifeedant effect of polygodial and drimenol derivatives against Spodoptera frugiperda and Epilachna paenulata and quantitative structure-activity analysis. Pest Manag Sci. 2018 Jul;74(7):1623-1629. doi: 10.1002/ps.4853. Epub 2018 Mar 2. PubMed PMID: 29316155. 14: Ding ZG, Zhao JY, Ding JH, Chunyu WX, Li MG, Gu SJ, Wang F, Wen ML. A novel phenylspirodrimane dimer from cultures of the fungus Stachybotrys chartarum. Nat Prod Res. 2018 Oct;32(19):2370-2374. doi: 10.1080/14786419.2017.1413565. Epub 2017 Dec 18. PubMed PMID: 29252003. 15: Li D, Zhang S, Song Z, Li W, Zhu F, Zhang J, Li S. Synthesis and bio-inspired optimization of drimenal: Discovery of chiral drimane fused oxazinones as promising antifungal and antibacterial candidates. Eur J Med Chem. 2018 Jan 1;143:558-567. doi: 10.1016/j.ejmech.2017.11.051. Epub 2017 Nov 21. PubMed PMID: 29207338. 16: Carrasco H, Robles-Kelly C, Rubio J, Olea AF, Martínez R, Silva-Moreno E. Antifungal Effect of Polygodial on Botrytis cinerea, a Fungal Pathogen Affecting Table Grapes. Int J Mol Sci. 2017 Oct 27;18(11). pii: E2251. doi: 10.3390/ijms18112251. PubMed PMID: 29077000; PubMed Central PMCID: PMC5713221. 17: Zhang S, Li D, Song Z, Zang C, Zhang L, Song X, Li S. "Carbon Assimilation" Inspired Design and Divergent Synthesis of Drimane Meroterpenoid Mimics as Novel Fungicidal Leads. J Agric Food Chem. 2017 Oct 18;65(41):9013-9021. doi: 10.1021/acs.jafc.7b03126. Epub 2017 Oct 5. PubMed PMID: 28949528. 18: Tang MC, Cui X, He X, Ding Z, Zhu T, Tang Y, Li D. Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Org Lett. 2017 Oct 6;19(19):5376-5379. doi: 10.1021/acs.orglett.7b02653. Epub 2017 Sep 19. PubMed PMID: 28926261; PubMed Central PMCID: PMC5682560. 19: Robles-Kelly C, Rubio J, Thomas M, Sedán C, Martinez R, Olea AF, Carrasco H, Taborga L, Silva-Moreno E. Effect of drimenol and synthetic derivatives on growth and germination of Botrytis cinerea: Evaluation of possible mechanism of action. Pestic Biochem Physiol. 2017 Sep;141:50-56. doi: 10.1016/j.pestbp.2016.11.006. Epub 2016 Nov 19. PubMed PMID: 28911740. 20: Mathie K, Lainer J, Spreng S, Dawid C, Andersson DA, Bevan S, Hofmann T. Structure-Pungency Relationships and TRP Channel Activation of Drimane Sesquiterpenes in Tasmanian Pepper (Tasmannia lanceolata). J Agric Food Chem. 2017 Jul 19;65(28):5700-5712. doi: 10.1021/acs.jafc.7b02356. Epub 2017 Jul 7. PubMed PMID: 28657737.