SCLAREOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H36O2
Molecular Weight	308.4986
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@](C)(O)[C@H](CC[C@@](C)(O)C=C)[C@@]1(C)CCCC2(C)C

InChI

InChIKey=XVULBTBTFGYVRC-HHUCQEJWSA-N

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

HIDE SMILES / InChI

Molecular Formula	C20H36O2
Molecular Weight	308.4986
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17260186
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22250858 https://www.ncbi.nlm.nih.gov/pubmed/27466023

Sclareol isolated from Salvia officinalis is widely used as a fragrance material. Sclareol is known to exert various biological activities. Sclareol possesses high lipophilicity, that precluded the evaluation of its anticancer effect in vivo. To overcome high toxicity and high lipophilicity of clareol, it was incorporated in liposomes. It demonstrated significant cytotoxic activity against human leukemic cell lines, but no cytotoxicity towards normal cells at concentration as high as 100 uM. Thus, sclareol possesses chemotherapeutic potential for the treatment of colorectal and other types of human cancer. Also was found, that sclareol-containing cream improved wrinkles in a clinical trial. It alleviates facial wrinkle formation via an antiphotoaging mechanism and may be an effective candidate ingredient. The anti-inflammatory mechanisms of sclareol might be related to a decrease of inflammatory cytokines and an increase of antioxidant enzyme activity.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17260186	Primary	Preclinical	Unknown Approved Use Unknown
Staphylococcal Infections 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17416571	Curative	Basic research	Unknown Approved Use Unknown
Pseudomonas infections 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17416571	Curative	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Diterpenes from the berries of Juniperus excelsa.	1999 Apr	10234860
The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol.	2002 Jun	12061897
Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.	2002 Oct	12237330
Pathogen-responsive expression of a putative ATP-binding cassette transporter gene conferring resistance to the diterpenoid sclareol is regulated by multiple defense signaling pathways in Arabidopsis.	2003 Nov	14526118
Effect of 13-epi-sclareol on the bacterial respiratory chain.	2004 Nov	15549662
First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol.	2005 Apr 14	15816731
A comparative study of the effects of cholesterol and sclareol, a bioactive labdane type diterpene, on phospholipid bilayers.	2005 Feb	15642582
Labd-14-ene-8,13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs.	2006 Apr	16527443
Hemisynthesis of new labdane derivatives from (-)-sclareol.	2006 Aug	16854715
Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts.	2006 Jan	16253514
Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice.	2007 Apr	17260186
Fragrance material review on sclareol.	2008 Nov	18640178
Hemisynthesis of two marine cheilanthane sesterterpenes from (-)-sclareol: first enantioselective synthesis of petrosaspongiolide R.	2009	19235026
Sclareol modulates the Treg intra-tumoral infiltrated cell and inhibits tumor growth in vivo.	2010	20409537
Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa.	2010 Aug	20839641
Identification and analysis of in planta expressed genes of Magnaporthe oryzae.	2010 Feb 10	20146797
Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol.	2010 Sep	19883213

Patents

Sample Use Guides

In Vivo Use Guide

immunodeficient SCID mice: liposome-encapsulated sclareol

Route of Administration: Intraperitoneal

In Vitro Use Guide

Sclareol triggers phospholipid scrambling of the erythrocyte cell membrane, an effect in part due to activation of p38 kinase and casein kinase 1α. A 48 hours exposure of human erythrocytes to Sclareol (≥ 50 µM) significantly increased the percentage of annexin-V-binding cells without significantly modifying the average forward scatter. Sclareol (100 µM) significantly increased Fluo3-fluorescence, but the effect of Sclareol on annexin-V-binding was not significantly blunted by removal of extracellular Ca2+. Instead, the effect of Sclareol on annexin-V-binding was significantly blunted in the presence of p38 kinase inhibitor skepinone (2 µM) and in the presence of casein kinase 1α inhibitor D4476 (10 µM).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 20:08:58 GMT 2023` Edited by `admin` on `Sat Dec 16 20:08:58 GMT 2023`
Record UNII	B607NP0Q8Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCLAREOL

Official Name

English

LABD-14-ENE-8,13-DIOL, (13R)-

Common Name

English

1-NAPHTHALENEPROPANOL, .ALPHA.-ETHENYLDECAHYDRO-2-HYDROXY-.ALPHA.,2,5,5,8A-PENTAMETHYL-, (1R-(1.ALPHA.(R*),2.BETA.,4A.BETA.,8A.ALPHA.))-

Common Name

English

FEMA NO. 4502

Code

English

1-NAPHTHALENEPROPANOL, .ALPHA.-ETHENYLDECAHYDRO-2-HYDROXY-.ALPHA.,2,5,5,8A-PENTAMETHYL-, (.ALPHA.R,1R,2R,4AS,8AS)-

Common Name

English

SCLAREOL [INCI]

Common Name

English

(-)-SCLAREOL

Common Name

English

Classification Tree Code System Code

EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION

SCCS/1459/11