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358002

Sigma-Aldrich

(3aR)-(+)-Sclareolide

97%

Synonym(s):

(+)-Norambreinolide

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About This Item

Empirical Formula (Hill Notation):
C16H26O2
CAS Number:
564-20-5
Molecular Weight:
250.38
EC Number:
209-269-0
MDL number:
MFCD00134168
UNSPSC Code:
12352005
PubChem Substance ID:
24861957
NACRES:
NA.22

Quality Level

100

Assay

97%

form

powder

optical activity

[α]20/D +47°, c = 2% in chloroform

mp

124-126 °C (lit.)

SMILES string

[H][C@@]12CC[C@@]3(C)OC(=O)C[C@]3([H])[C@@]1(C)CCCC2(C)C

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

InChI key

IMKJGXCIJJXALX-SHUKQUCYSA-N

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General description

Sclareolide is a diterpenoid compound mainly used in the perfume industry for its amber like odor.

Application

(3aR)-(+)-Sclareolide may be used in the total syntheses of bioactive compounds such as (+)-chloropuupehenone, (+)-chloropuupehenol, cyslabdan, acuminolide and 17-O-acetylacuminolide. It may also be used in the preparation of γ-bicyclohomofarnesal, an ambergris odorant.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBS9199V
MKBP9663V
MKBP8275V
MKBP3189V
MKBP1027V

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Synthesis of Acuminolide and 17-O-Acetylacuminolide from (+)-Sclareolide.
Zoretic PA, et al.
The Journal of Organic Chemistry, 63(4), 1156-1161 (1998)
Superacid cyclization of homo-and bishomoisoprenoid acids.
Vlad PF, et al.
Chemistry of Heterocyclic Compounds, 27(3), 246-249 (1991)
Total syntheses of (+)-chloropuupehenone and (+)-chloropuupehenol and their analogues and evaluation of their bioactivities.
Hua DH, et al.
The Journal of Organic Chemistry, 69(18), 6065-6078 (2004)
Natural sesquiterpenoids.
Fraga BM.
Natural Product Reports, 20(4), 392-413 (2003)
Synthesis and Structural Revision of Cyslabdan.
Ohtawa M, et al.
Chemical & Pharmaceutical Bulletin, 64(9), 1370-1377 (2016)

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