Sclareol | CAS#515-03-7 | diterpene compound

MedKoo Cat#: 598173 | Name: Sclareol

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Description:

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

Sclareol is a diterpene compound with a labdane skeleton, is mainly used as a raw material in the fragrance industry. It shows potent cytotoxic and cytostatic effect in human leukemic cell lines.

Chemical Structure

Sclareol

CAS#515-03-7

Theoretical Analysis

MedKoo Cat#: 598173

Name: Sclareol

CAS#: 515-03-7

Chemical Formula: C20H36O2

Exact Mass: 308.2715

Molecular Weight: 308.50

Elemental Analysis: C, 77.87; H, 11.76; O, 10.37

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 weeks
25g	USD 550.00	2 Weeks

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Related CAS #

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Synonym

Sclareol;

IUPAC/Chemical Name

(1R,2R,4aS,8aS)-1-((R)-3-hydroxy-3-methylpent-4-en-1-yl)-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol

InChi Key

XVULBTBTFGYVRC-HHUCQEJWSA-N

InChi Code

InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1

SMILES Code

C[C@@](CC[C@H]1[C@](O)(CC[C@H]2C(C)(CCC[C@]12C)C)C)(C=C)O

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sclareol is isolated from Salvia sclarea with anticarcinogenic activity. Sclareol shows strong cytotoxic activity against mouse leukemia (P-388), human epidermal carcinoma (KB) cells and human leukemia cell lines. Sclareol induces cell apoptosis.

In vitro activity:

The results of this study suggest that sclareol can reduce lung carcinoma cell growth and metastasis and promote cell death. In A549 cells, sclareol treatment inhibited clonogenic features and reduced their migration and invasion potential in a dose-dependent manner. Sclareol treatment downregulated the expression of cyclin D1 and survivin and upregulated that of p21 and p16. Reference: J Biochem Mol Toxicol. 2023 Oct 18:e23563. https://pubmed.ncbi.nlm.nih.gov/37850667/

In vivo activity:

Sclareol has potential in the prevention of hypertensive heart failure. In a murine model of heart failure, sclareol administration significantly reduced the expression of myocardial injury markers. Sclareol also exerts protective effects against Ang II-induced cardiac dysfunction through inhibiting MAPK-mediated inflammation. Reference: Phytother Res. 2023 Feb;37(2):578-591. https://pubmed.ncbi.nlm.nih.gov/36178264/

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	162.07

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 308.50 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. Rah B, Shafarin J, Hamad M, Muhammad JS. Sclareol induces cell cycle arrest and ROS-mediated apoptosis and ferroptosis in lung adenocarcinoma cells. J Biochem Mol Toxicol. 2023 Oct 18:e23563. doi: 10.1002/jbt.23563. Epub ahead of print. PMID: 37850667. 2. Kim C, Kim JG, Kim KY. Anti-Candida Potential of Sclareol in Inhibiting Growth, Biofilm Formation, and Yeast-Hyphal Transition. J Fungi (Basel). 2023 Jan 10;9(1):98. doi: 10.3390/jof9010098. PMID: 36675919; PMCID: PMC9862543. 3. Ge MX, Niu WX, Bao YY, Lu ZN, He HW. Sclareol attenuates liver fibrosis through SENP1-mediated VEGFR2 SUMOylation and inhibition of downstream STAT3 signaling. Phytother Res. 2023 Sep;37(9):3898-3912. doi: 10.1002/ptr.7845. Epub 2023 May 2. PMID: 37132081. 4. Yang N, Zou C, Luo W, Xu D, Wang M, Wang Y, Wu G, Shan P, Liang G. Sclareol attenuates angiotensin II-induced cardiac remodeling and inflammation via inhibiting MAPK signaling. Phytother Res. 2023 Feb;37(2):578-591. doi: 10.1002/ptr.7635. Epub 2022 Sep 30. PMID: 36178264.

In vitro protocol:

In vivo protocol:

1. Ge MX, Niu WX, Bao YY, Lu ZN, He HW. Sclareol attenuates liver fibrosis through SENP1-mediated VEGFR2 SUMOylation and inhibition of downstream STAT3 signaling. Phytother Res. 2023 Sep;37(9):3898-3912. doi: 10.1002/ptr.7845. Epub 2023 May 2. PMID: 37132081. 2. Yang N, Zou C, Luo W, Xu D, Wang M, Wang Y, Wu G, Shan P, Liang G. Sclareol attenuates angiotensin II-induced cardiac remodeling and inflammation via inhibiting MAPK signaling. Phytother Res. 2023 Feb;37(2):578-591. doi: 10.1002/ptr.7635. Epub 2022 Sep 30. PMID: 36178264.

1: Zhong Y, Huang Y, Santoso MB, Wu LD. Sclareol exerts anti-osteoarthritic activities in interleukin-1β-induced rabbit chondrocytes and a rabbit osteoarthritis model. Int J Clin Exp Pathol. 2015 Mar 1;8(3):2365-74. eCollection 2015. PubMed PMID: 26045743; PubMed Central PMCID: PMC4440052. 2: Fujimoto T, Mizukubo T, Abe H, Seo S. Sclareol induces plant resistance to root-knot nematode partially through ethylene-dependent enhancement of lignin accumulation. Mol Plant Microbe Interact. 2015 Apr;28(4):398-407. doi: 10.1094/MPMI-10-14-0320-R. PubMed PMID: 25423264. 3: Wang L, He HS, Yu HL, Zeng Y, Han H, He N, Liu ZG, Wang ZY, Xu SJ, Xiong M. Sclareol, a plant diterpene, exhibits potent antiproliferative effects via the induction of apoptosis and mitochondrial membrane potential loss in osteosarcoma cancer cells. Mol Med Rep. 2015 Jun;11(6):4273-8. doi: 10.3892/mmr.2015.3325. Epub 2015 Feb 10. PubMed PMID: 25672419. 4: Signoretto E, Laufer SA, Lang F. Stimulating Effect of Sclareol on Suicidal Death of Human Erythrocytes. Cell Physiol Biochem. 2016;39(2):554-64. doi: 10.1159/000445647. Epub 2016 Jul 11. PubMed PMID: 27395049. 5: 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. 6: Noori S, Hassan ZM, Salehian O. Sclareol reduces CD4+ CD25+ FoxP3+ Treg cells in a breast cancer model in vivo. Iran J Immunol. 2013 Mar;10(1):10-21. doi: IJIv10i1A2. PubMed PMID: 23502334. 7: Park JE, Lee KE, Jung E, Kang S, Kim YJ. Sclareol isolated from Salvia officinalis improves facial wrinkles via an antiphotoaging mechanism. J Cosmet Dermatol. 2016 Dec;15(4):475-483. doi: 10.1111/jocd.12239. Epub 2016 Jul 28. PubMed PMID: 27466023. 8: Trikka FA, Nikolaidis A, Athanasakoglou A, Andreadelli A, Ignea C, Kotta K, Argiriou A, Kampranis SC, Makris AM. Iterative carotenogenic screens identify combinations of yeast gene deletions that enhance sclareol production. Microb Cell Fact. 2015 Apr 24;14:60. doi: 10.1186/s12934-015-0246-0. PubMed PMID: 25903744; PubMed Central PMCID: PMC4413541. 9: Shakeel-u-Rehman, Rah B, Lone SH, Rasool RU, Farooq S, Nayak D, Chikan NA, Chakraborty S, Behl A, Mondhe DM, Goswami A, Bhat KA. Design and Synthesis of Antitumor Heck-Coupled Sclareol Analogues: Modulation of BH3 Family Members by SS-12 in Autophagy and Apoptotic Cell Death. J Med Chem. 2015 Apr 23;58(8):3432-44. doi: 10.1021/jm501942m. Epub 2015 Apr 9. PubMed PMID: 25825934. 10: Ouyang P, Sun M, He X, Wang K, Yin Z, Fu H, Li Y, Geng Y, Shu G, He C, Liang X, Lai W, Li L, Zou Y, Song X, Yin L. Sclareol protects Staphylococcus aureus-induced lung cell injury via inhibiting alpha-hemolysin expression. J Microbiol Biotechnol. 2016 Sep 23. doi: 10.4014/jmb.1606.06039. [Epub ahead of print] PubMed PMID: 27666983. 11: Yang W, Zhou Y, Liu W, Shen H, Zhao ZK. [Engineering Saccharomyces cerevisiae for sclareol production]. Sheng Wu Gong Cheng Xue Bao. 2013 Aug;29(8):1185-92. Chinese. PubMed PMID: 24364354. 12: Ma M, Feng J, Li R, Chen SW, Xu H. Synthesis and antifungal activity of ethers, alcohols, and iodohydrin derivatives of sclareol against phytopathogenic fungi in vitro. Bioorg Med Chem Lett. 2015 Jul 15;25(14):2773-7. doi: 10.1016/j.bmcl.2015.05.013. Epub 2015 May 14. PubMed PMID: 26013848. 13: Song Y, Shen H, Yang W, Yang X, Gong Z, Zhao ZK. [High cell density culture of an engineered yeast strain for sclareol production]. Sheng Wu Gong Cheng Xue Bao. 2015 Jan;31(1):147-51. Chinese. PubMed PMID: 26021088. 14: Schalk M, Pastore L, Mirata MA, Khim S, Schouwey M, Deguerry F, Pineda V, Rocci L, Daviet L. Toward a biosynthetic route to sclareol and amber odorants. J Am Chem Soc. 2012 Nov 21;134(46):18900-3. doi: 10.1021/ja307404u. Epub 2012 Nov 7. PubMed PMID: 23113661. 15: Chain FE, Leyton P, Paipa C, Fortuna M, Brandán SA. FT-IR, FT-Raman, UV-visible, and NMR spectroscopy and vibrational properties of the labdane-type diterpene 13-epi-sclareol. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Mar 5;138:303-13. doi: 10.1016/j.saa.2014.11.049. Epub 2014 Nov 29. PubMed PMID: 25498827. 16: Caniard A, Zerbe P, Legrand S, Cohade A, Valot N, Magnard JL, Bohlmann J, Legendre L. Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture. BMC Plant Biol. 2012 Jul 26;12:119. doi: 10.1186/1471-2229-12-119. PubMed PMID: 22834731; PubMed Central PMCID: PMC3520730. 17: Mahaira LG, Tsimplouli C, Sakellaridis N, Alevizopoulos K, Demetzos C, Han Z, Pantazis P, Dimas K. The labdane diterpene sclareol (labd-14-ene-8, 13-diol) induces apoptosis in human tumor cell lines and suppression of tumor growth in vivo via a p53-independent mechanism of action. Eur J Pharmacol. 2011 Sep;666(1-3):173-82. doi: 10.1016/j.ejphar.2011.04.065. Epub 2011 May 20. PubMed PMID: 21620827. 18: Bouanou H, Gil JA, Alvarez-Manzaneda R, Chahboun R, Alvarez-Manzaneda E. Oxidative Coupling of (-)-Sclareol and Related Diols Leading to Oxepane Terpenoids. J Org Chem. 2016 Oct 21;81(20):10002-10008. Epub 2016 Oct 7. PubMed PMID: 27689238. 19: Caissard JC, Olivier T, Delbecque C, Palle S, Garry PP, Audran A, Valot N, Moja S, Nicolé F, Magnard JL, Legrand S, Baudino S, Jullien F. Extracellular localization of the diterpene sclareol in clary sage (Salvia sclarea L., Lamiaceae). PLoS One. 2012;7(10):e48253. doi: 10.1371/journal.pone.0048253. Epub 2012 Oct 25. PubMed PMID: 23133579; PubMed Central PMCID: PMC3484996. 20: Noori S, Hassan ZM, Mohammadi M, Habibi Z, Sohrabi N, Bayanolhagh S. Sclareol modulates the Treg intra-tumoral infiltrated cell and inhibits tumor growth in vivo. Cell Immunol. 2010;263(2):148-53. doi: 10.1016/j.cellimm.2010.02.009. Epub 2010 Mar 10. PubMed PMID: 20409537.