SCLAREOLIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H26O2
Molecular Weight	250.3764
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12CC[C@H]3C(C)(C)CCC[C@]3(C)[C@H]1CC(=O)O2

InChI

InChIKey=IMKJGXCIJJXALX-SHUKQUCYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17416571
Curator's Comment: description was created based on several sources, including US Patent Application No. 2010/0183527 A1

Sclareolide is a sesquiterpene lactone natural product derived from various plant sources including Salvia sclarea, Salvia yosgadensis, and cigar tobacco. Sclareolide demonstrated good antibacterial activity against common human pathogens, including Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and Enterococcus faecalis. Sclareolide is not generally known for its bioactive properties. Instead, it is mostly used as a fixative or base in the perfume industry. It is also used in cosmetics, because it is thought to contribute to tanning of skin and/or darkening of hair.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Staphylococcal infections 24 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
Manganese porphyrins catalyze selective C-H bond halogenations.	2010-09-22	20806921
Synthesis and biological evaluation of (+)-labdadienedial, derivatives and precursors from (+)-sclareolide.	2010-09	20619938
Enantiospecific, biosynthetically inspired formal total synthesis of (+)-liphagal.	2010-05-21	20394432
Identification and analysis of in planta expressed genes of Magnaporthe oryzae.	2010-02-10	20146797
Differential enhancement of leukaemia cell differentiation without elevation of intracellular calcium by plant-derived sesquiterpene lactone compounds.	2008-11	18724384
Structure revision and synthesis of a novel labdane diterpenoid from Zingiber ottensii.	2008-08-21	18616256
(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetra-methyl-2-oxoperhydro-naphtho[2,1-b]furan-7-yl acetate.	2008-08-16	21201747
Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products.	2007-04	17416571
Novel microbial transformations of sclareolide.	2007-01	17202714
The nicholas approach to natural product hybrids.	2006-08-16	16741909
Synthesis and biological activity of (+)-hedychilactone A and its analogs from (+)-sclareolide.	2006-03-15	16384699
Synthesis of alpha-onoceradiene-like terpene dimers by intermolecular metathesis processes.	2006-02-16	16468719
Diversity oriented synthesis of hispanane-like terpene derivatives from (R)-(+)-sclareolide.	2005-06-06	15812873
Synthesis of pelorol and analogues: activators of the inositol 5-phosphatase SHIP.	2005-03-17	15760142
Photochemical access to tetra- and pentacyclic terpene-like products from R-(+)-sclareolide.	2003-08-22	12919024
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
A study on the synthesis of antiangiogenic (+)-coronarin A and congeners from (+)-sclareolide.	2003-06-16	12781184
Enantiospecific synthesis of the antituberculosis marine sponge metabolite (+)-puupehenone. The arenol oxidative activation route.	2002-10-31	12599506
The ABC transporter SpTUR2 confers resistance to the antifungal diterpene sclareol.	2002-06	12061897
An approach to furolabdanes and their photooxidation derivatives from R-(+)-sclareolide.	2002-05	12027737
Total synthesis and determination of the absolute configuration of coscinosulfate. A new selective inhibitor of Cdc25 protein phosphatase.	2001-11-02	11681936
A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion.	2001-05	11340184

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

SCLAREOLIDE

Official Name

English

FEMA NO. 3794

Preferred Name

English

NORAMBREINOLIDE

Common Name

English

NAPHTHO(2,1-B)FURAN-2(1H)-ONE, DECAHYDRO-3A,6,6,9A-TETRAMETHYL-, (3AR,5AS,9AS,9BR)-

Common Name

English

(3AR)-(+)-SCLAREOLIDE

Common Name

English

SCLAREOLIDE [FHFI]

Common Name

English

12-NORAMBREINOLIDE

Common Name

English

Classification Tree Code System Code

DSLD

3501 (Number of products:2)