Sclareolide | CAS#564-20-5 | sesquiterpene lactone

MedKoo Cat#: 461938 | Name: Sclareolide

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Description:

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

Sclareolide is a sesquiterpene lactone natural product derived from various plant sources. It is a close analog of sclareol, a plant antifungal compound.

Chemical Structure

Sclareolide

CAS#564-20-5

Theoretical Analysis

MedKoo Cat#: 461938

Name: Sclareolide

CAS#: 564-20-5

Chemical Formula: C16H26O2

Exact Mass: 250.1933

Molecular Weight: 250.38

Elemental Analysis: C, 76.75; H, 10.47; O, 12.78

Price and Availability

Size	Price	Availability	Quantity
5g	USD 285.00	2 weeks

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Related CAS #

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Synonym

Sclareolide; Norambreinolide;

IUPAC/Chemical Name

(3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldecahydronaphtho[2,1-b]furan-2(1H)-one

InChi Key

IMKJGXCIJJXALX-SHUKQUCYSA-N

InChi Code

InChI=1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1

SMILES Code

O=C1C[C@@]2([H])[C@](CC[C@@]3([H])C(C)(C)CCC[C@@]32C)(C)O1

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 and water

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sclareolide inhibits mycelial growth in the phytopathogenic fungi B. cinerea, F. coeruleum, C. lunata, F. graminearum, and A. brassicae by 33.93, 67.14, 27.04, 46.22, and 32.48%, respectively. Sclareolide is an Ebola virus entry inhibitor that reduces infection of HEK293T cells by an HIV-based virus system pseudotyped with Ebola virus glycoprotein (EC50 = 8 μM). It inhibits nitric oxide production in LPS-stimulated BV-2 cells (IC50 = 20.3 μM). Sclareolide enhances gemcitabine-induced cell death in gemcitabine-resistant PANC-1 and AsPC-1 human pancreatic cancer cells.

In vitro activity:

Sclareolide may be a novel agent in combination with gemcitabine for the treatment of gemcitabine‑resistant pancreatic cancer. Sclareolide resensitized gemcitabine‑resistant cells (GR‑HPCCs) to gemcitabine through inducing apoptosis. Sclareolide upregulated hENT1, downregulated RRM1 and inhibited gemcitabine‑induced epithelial to mesenchymal transition through the TWIST1/Slug pathway in the GR‑HPCCs. Reference: Mol Med Rep. 2017 Apr;15(4):1461-1470. https://pubmed.ncbi.nlm.nih.gov/28259943/

In vivo activity:

To be determined

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	399.39
	Water	0.1	0.40

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 250.38 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

Formulation protocol:

1. Chen S, Wang Y, Zhang WL, Dong MS, Zhang JH. Sclareolide enhances gemcitabine‑induced cell death through mediating the NICD and Gli1 pathways in gemcitabine‑resistant human pancreatic cancer. Mol Med Rep. 2017 Apr;15(4):1461-1470. doi: 10.3892/mmr.2017.6182. Epub 2017 Feb 8. PMID: 28259943; PMCID: PMC5365005. 2. Hayet E, Fatma B, Souhir I, Waheb FA, Abderaouf K, Mahjoub A, Maha M. Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products. Pak J Pharm Sci. 2007 Apr;20(2):146-8. PMID: 17416571.

In vitro protocol:

In vivo protocol:

To be determined

1: Martins MP, Ouazzani J, Arcile G, Jeller AH, de Lima JP, Seleghim MH, Oliveira AL, Debonsi HM, Venâncio T, Yokoya NS, Fujii MT, Porto AL. Biohydroxylation of (-)-ambrox®, (-)-sclareol, and (+)-sclareolide by whole cells of Brazilian marine-derived fungi. Mar Biotechnol (NY). 2015 Apr;17(2):211-8. doi: 10.1007/s10126-015-9610-7. Epub 2015 Jan 30. PubMed PMID: 25634054. 2: Kumar CN, Chein RJ. Synthesis of labdane diterpenes galanal A and B from (+)-sclareolide. Org Lett. 2014 Jun 6;16(11):2990-2. doi: 10.1021/ol501121v. Epub 2014 May 5. PubMed PMID: 24797451. 3: Dixon DD, Lockner JW, Zhou Q, Baran PS. Scalable, divergent synthesis of meroterpenoids via "borono-sclareolide". J Am Chem Soc. 2012 May 23;134(20):8432-5. doi: 10.1021/ja303937y. Epub 2012 May 14. PubMed PMID: 22583115. 4: Nagaraju K, Chegondi R, Chandrasekhar S. Expanding Diversity without Protecting Groups: (+)-Sclareolide to Indolosesquiterpene Alkaloid Mycoleptodiscin A and Analogues. Org Lett. 2016 Jun 3;18(11):2684-7. doi: 10.1021/acs.orglett.6b01145. Epub 2016 May 16. PubMed PMID: 27181938. 5: Farooq A, Tahara S. Oxidative metabolism of ambrox and sclareolide by Botrytis cinerea. Z Naturforsch C. 2000 May-Jun;55(5-6):341-6. PubMed PMID: 10928544. 6: Rajsz A, Warzybok A, Migocka M. Genes Encoding Cucumber Full-Size ABCG Proteins Show Different Responses to Plant Growth Regulators and Sclareolide. Plant Mol Biol Report. 2016;34:720-736. Epub 2015 Nov 14. PubMed PMID: 27429510; PubMed Central PMCID: PMC4923091. 7: Ata A, Conci LJ, Betteridge J, Orhan I, Sener B. Novel microbial transformations of sclareolide. Chem Pharm Bull (Tokyo). 2007 Jan;55(1):118-23. PubMed PMID: 17202714. 8: Riofski MV, John JP, Zheng MM, Kirshner J, Colby DA. Exploiting the facile release of trifluoroacetate for the α-methylenation of the sterically hindered carbonyl groups on (+)-sclareolide and (-)-eburnamonine. J Org Chem. 2011 May 20;76(10):3676-83. doi: 10.1021/jo102114f. Epub 2011 Apr 14. PubMed PMID: 21491928. 9: Atta-ur-Rahman, Farooq A, Choudhary MI. Microbial transformation of sclareolide. J Nat Prod. 1997 Oct;60(10):1038-40. PubMed PMID: 9358647. 10: Oh S, Jeong IH, Shin WS, Lee S. A study on the synthesis of antiangiogenic (+)-coronarin A and congeners from (+)-sclareolide. Bioorg Med Chem Lett. 2003 Jun 16;13(12):2009-12. PubMed PMID: 12781184. 11: González MA, Mancebo-Aracil J, Tangarife-Castaño V, Agudelo-Goméz L, Zapata B, Mesa-Arango A, Betancur-Galvis L. Synthesis and biological evaluation of (+)-labdadienedial, derivatives and precursors from (+)-sclareolide. Eur J Med Chem. 2010 Sep;45(9):4403-8. doi: 10.1016/j.ejmech.2010.06.029. Epub 2010 Jun 25. PubMed PMID: 20619938. 12: de la Torre MC, García I, Sierra MA. Diversity oriented synthesis of hispanane-like terpene derivatives from (R)-(+)-sclareolide. Chemistry. 2005 Jun 6;11(12):3659-67. PubMed PMID: 15812873. 13: Oh S, Jeong IH, Shin WS, Wang Q, Lee S. Synthesis and biological activity of (+)-hedychilactone A and its analogs from (+)-sclareolide. Bioorg Med Chem Lett. 2006 Mar 15;16(6):1656-9. Epub 2005 Dec 27. PubMed PMID: 16384699. 14: De la Torre MC, García I, Sierra MA. An approach to furolabdanes and their photooxidation derivatives from R-(+)-sclareolide. J Nat Prod. 2002 May;65(5):661-8. PubMed PMID: 12027737. 15: de la Torre MC, García I, Sierra MA. Photochemical access to tetra- and pentacyclic terpene-like products from R-(+)-sclareolide. J Org Chem. 2003 Aug 22;68(17):6611-8. PubMed PMID: 12919024. 16: Shi XW, Li SK, Li DD, Lu QQ. Crystal structure of 3a,6,6,9a-tetra-methyl-dodeca-hydro-naphtho-[2,1-b]furan-2-ol. Acta Crystallogr E Crystallogr Commun. 2015 Sep 12;71(Pt 10):o710-1. doi: 10.1107/S2056989015016370. eCollection 2015 Oct 1. PubMed PMID: 26594436; PubMed Central PMCID: PMC4647384. 17: Li DD, Shi XW, Lu QQ, Li SK. Crystal structure of 2-[(1R,2R,4aS,8aS)-2-hy-droxy-2,5,5,8a-tetra-methyl-deca-hydro-naphthalen-1-yl]-N -(o-tol-yl)acetamide. Acta Crystallogr E Crystallogr Commun. 2015 Sep 26;71(Pt 10):o788-9. doi: 10.1107/S2056989015017600. eCollection 2015 Oct 1. PubMed PMID: 26594480; PubMed Central PMCID: PMC4647428. 18: Kakde BN, Kumar N, Mondal PK, Bisai A. Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A. Org Lett. 2016 Apr 15;18(8):1752-5. doi: 10.1021/acs.orglett.6b00446. Epub 2016 Mar 30. PubMed PMID: 27028314. 19: Deng H, Cao W, Zhang Z, Liu B. Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis. Org Biomol Chem. 2016 Jul 14;14(26):6225-30. doi: 10.1039/c6ob00750c. Epub 2016 Jun 2. PubMed PMID: 27251032. 20: Chen S, Wang Y, Zhang WL, Dong MS, Zhang JH. Sclareolide enhances gemcitabine induced cell death through mediating the NICD and Gli1 pathways in gemcitabine resistant human pancreatic cancer. Mol Med Rep. 2017 Apr;15(4):1461-1470. doi: 10.3892/mmr.2017.6182. Epub 2017 Feb 8. PubMed PMID: 28259943; PubMed Central PMCID: PMC5365005.