Sclareol

Names

[ CAS No. ]:
515-03-7

[ Name ]:
Sclareol

[Synonym ]:
(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-methyl-4-penten-1-yl]-2,5,5,8a-tetramethyldecahydro-2-naphthalenol
(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol
SCLAREOL(RG)
EINECS 208-194-0
1-Naphthalenepropanol, α-ethenyldecahydro-2-hydroxy-α,2,5,5,8a-pentamethyl-, (αR,1R,2R,4aS,8aS)-
Labd-14-ene-8,13-diol, (13R)-
SCIADONIC ACID
(1R,2R,8aS)-Decahydro-1-(3-hydroxy-3-methyl-4-pentenyl)-2,5,5,8a-tetramethyl-2-naphthol
labd-14-ene-8,13(R)-diol
MFCD00869558
SCLAREOL,NATURAL
SCAREOL
Sclareol
(-)-sclareol
SCLAREOL(P)
(1R,2R,4aS,8aS)-1-[(3R)-3-Hydroxy-3-méthyl-4-pentèn-1-yl]-2,5,5,8a-tétraméthyldécahydro-2-naphtalénol

Biological Activity

[Description]:

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[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[In Vitro]

Sclareol is cytotoxic to 13 of 14 human leukemia cell lines tested, with IC50 values ranging from 6.0–24.2 μg/mL, but is not cytotoxic to peripheral blood mononuclear leukocytes within the same dose range[1].

[References]

[1]. Robert Tisserand, et al. Sclareol.Constituent profiles

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
398.3±15.0 °C at 760 mmHg

[ Melting Point ]:
95-100 °C(lit.)

[ Molecular Formula ]:
C₂₀H₃₆O₂

[ Molecular Weight ]:
308.499

[ Flash Point ]:
169.1±15.0 °C

[ Exact Mass ]:
308.271515

[ PSA ]:
40.46000

[ LogP ]:
5.54

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.490

[ Storage condition ]:
2-8C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QK0301900

CHEMICAL NAME :: 1-Naphthalenepropanol, decahydro-alpha-ethenyl-2-hydroxy-alpha,2,5,5,8a-pent amethyl-, (1R-(1-alpha(R*),2-beta,4a-beta,8a-alpha))-

CAS REGISTRY NUMBER :: 515-03-7

BEILSTEIN REFERENCE NO. :: 2054148

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C20-H36-O2

MOLECULAR WEIGHT :: 308.56

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 30,115S,1992

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 30,115S,1992

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
QK0301900

[ HS Code ]:
2906199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2906199090

[ Summary ]:
2906199090. cyclanic, cyclenic or cyclotherpenic alcohols. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

Articles

Parallel dual secondary column-dual detection: a further way of enhancing the informative potential of two-dimensional comprehensive gas chromatography.

J. Chromatogr. A. 1360 , 264-74, (2014)

Comprehensive two-dimensional gas chromatography (GC×GC) coupled with Mass Spectrometry (MS) is one of today's most powerful analytical platforms for detailed analysis of medium-to-high complexity sam...

Labdane diterpenoids from Salvia reuterana.

Phytochemistry 108 , 264-9, (2014)

Three labdane diterpenoids, 14α-hydroxy-15-chlorosclareol (1), 14α-hydroxy-15-acetoxysclareol (2), and 6β-hydroxy-14α-epoxysclareol (3), together with the known diterpenoids sclareol (4), 6β-hydroxysc...

Isolation, chemical, and biotransformation routes of labdane-type diterpenes.

Chem. Rev. 111(8) , 4418-52, (2011)