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

C[C@@](O)(CC[C@H]1[C@](C)(O)CC[C@H]2C(C)(C)CCC[C@]12C)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 66 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
A copal-8-ol diphosphate synthase from the angiosperm Cistus creticus subsp. creticus is a putative key enzyme for the formation of pharmacologically active, oxygen-containing labdane-type diterpenes.	2010-09	20595348
Mitochondria-targeted liposomes improve the apoptotic and cytotoxic action of sclareol.	2010-09	19883213
Chemical composition and antimicrobial activity of the essential oils from Cleome spinosa.	2010-08	20839641
Inhibition of angiogenesis- and inflammation-inducing factors in human colon cancer cells in vitro and in ovo by free and nanoparticle-encapsulated redox dye, DCPIP.	2010-07-15	20633276
Identification and analysis of in planta expressed genes of Magnaporthe oryzae.	2010-02-10	20146797
Sclareol modulates the Treg intra-tumoral infiltrated cell and inhibits tumor growth in vivo.	2010	20409537
Hemisynthesis of two marine cheilanthane sesterterpenes from (-)-sclareol: first enantioselective synthesis of petrosaspongiolide R.	2009	19235026
Fragrance material review on sclareol.	2008-11	18640178
Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro.	2007-10	17924309
Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products.	2007-04	17416571
Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice.	2007-04	17260186
Calorimetric study on the induction of interdigitated phase in hydrated DPPC bilayers by bioactive labdanes and correlation to their liposome stability: The role of chemical structure.	2007-01	17116297
Hemisynthesis of new labdane derivatives from (-)-sclareol.	2006-08	16854715
Liposomes modify the subcellular distribution of sclareol uptake by HCT-116 cancer cell lines.	2006-07-25	17270382
Synthesis of ent-thallusin.	2006-05-11	16671797
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.	2006-04	16527443
Structure elucidation and antibacterial activity of new fungal metabolites of sclareol.	2006-01	17193216
Cytotoxic and antitumor activity of liposome-incorporated sclareol against cancer cell lines and human colon cancer xenografts.	2006-01	16253514
NpPDR1, a pleiotropic drug resistance-type ATP-binding cassette transporter from Nicotiana plumbaginifolia, plays a major role in plant pathogen defense.	2005-09	16126865
Microbial hydroxylation of sclareol by Rhizopus stolonifer.	2005-08-31	18007369
First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol.	2005-04-14	15816731
A comparative study of the effects of cholesterol and sclareol, a bioactive labdane type diterpene, on phospholipid bilayers.	2005-02	15642582
Effect of 13-epi-sclareol on the bacterial respiratory chain.	2004-11	15549662
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.	2003-11	14526118
Identification of regulatory sequence elements within the transcription promoter region of NpABC1, a gene encoding a plant ABC transporter induced by diterpenes.	2003-07	12848828
Antibacterial diterpenoids from Astragalus brachystachys.	2003-02-04	12562087
The plant PDR family of ABC transporters.	2002-11	12430018
Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.	2002-10	12237330
The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol.	2002-06	12061897
Antimycobacterial plant terpenoids.	2001-11	11731906
A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion.	2001-05	11340184
Chromatographic (GC-MS, HPLC) and virological evaluations of Salvia sclarea infected by BBWV-I.	2001-03	11409330
Diterpenes from the berries of Juniperus excelsa.	1999-04	10234860

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 `Wed Apr 02 18:19:45 GMT 2025` Edited by `admin` on `Wed Apr 02 18:19:45 GMT 2025`
Record UNII	B607NP0Q8Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FEMA NO. 4502

Preferred Name

English

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

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

Common Name

English

(-)-SCLAREOL

Common Name

English

Classification Tree Code System Code

EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION

SCCS/1459/11