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

[H][C@]12CC(=O)O[C@]1(C)CC[C@@]3([H])C(C)(C)CCC[C@]23C

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

Molecular Formula	C16H26O2
Molecular Weight	250.3764
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Total synthesis and determination of the absolute configuration of coscinosulfate. A new selective inhibitor of Cdc25 protein phosphatase.	2001 Nov 2	11681936
Enantiospecific synthesis of the antituberculosis marine sponge metabolite (+)-puupehenone. The arenol oxidative activation route.	2002 Oct 31	12599506
Diversity oriented synthesis of hispanane-like terpene derivatives from (R)-(+)-sclareolide.	2005 Jun 6	15812873
Synthesis of pelorol and analogues: activators of the inositol 5-phosphatase SHIP.	2005 Mar 17	15760142
The nicholas approach to natural product hybrids.	2006 Aug 16	16741909
Synthesis of alpha-onoceradiene-like terpene dimers by intermolecular metathesis processes.	2006 Feb 16	16468719
Synthesis and biological activity of (+)-hedychilactone A and its analogs from (+)-sclareolide.	2006 Mar 15	16384699
Antibacterial and cytotoxic activity of the acetone extract of the flowers of Salvia sclarea and some natural products.	2007 Apr	17416571
Novel microbial transformations of sclareolide.	2007 Jan	17202714
(3aS,7S,9aS,9bR)-3a,6,6,9a-Tetra-methyl-2-oxoperhydro-naphtho[2,1-b]furan-7-yl acetate.	2008 Aug 16	21201747
Structure revision and synthesis of a novel labdane diterpenoid from Zingiber ottensii.	2008 Aug 21	18616256
Differential enhancement of leukaemia cell differentiation without elevation of intracellular calcium by plant-derived sesquiterpene lactone compounds.	2008 Nov	18724384
Identification and analysis of in planta expressed genes of Magnaporthe oryzae.	2010 Feb 10	20146797
Enantiospecific, biosynthetically inspired formal total synthesis of (+)-liphagal.	2010 May 21	20394432
Synthesis and biological evaluation of (+)-labdadienedial, derivatives and precursors from (+)-sclareolide.	2010 Sep	20619938
Manganese porphyrins catalyze selective C-H bond halogenations.	2010 Sep 22	20806921

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:17:26 GMT 2023` Edited by `admin` on `Fri Dec 15 17:17:26 GMT 2023`
Record UNII	37W4O0O6E6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCLAREOLIDE

Official Name

English

SCLAREOLIDE [INCI]

Common 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

FEMA NO. 3794

Code

English

Classification Tree Code System Code

DSLD

3501 (Number of products:2)