6750-60-3

Usage

Appearance

Spathulenol is a colorless to pale yellow clear liquid.

Biological activity

Spathulenol is isolated from psidium guineense Sw, has antioxidant, anti-inflammatory, anti-proliferative and anti-mycobacterial activities. It shows high antioxidant activity in DPPH system with IC50 of 85.60 μg/mL.

Uses

Eucalyptol is an organic alcohol compound, mainly used for content determination and experimental research, not for other purposes.

InChI:InChI=1/C15H24O/c1-9-5-6-11-13(14(11,2)3)12-10(9)7-8-15(12,4)16/h10-13,16H,1,5-8H2,2-4H3/t10-,11+,12+,13+,15-/m0/s1

Upstream product

• 99147-42-9 (+)-11β-hydroxy-apoaromadendrone 
• 19493-09-5 Methylenetriphenylphosphorane 
• 2344-80-1 Chloromethyltrimethylsilane 
• 32543-79-6 (1S,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropane-1-carbaldehyde 
• 4497-92-1 2-carene 
• 41437-00-7 (+)-bicyclogermacrene 
• 489-39-4 (+)-aromadendrene 
• 99147-41-8 (1aR,4aR,7R,7aS,7bS)-1,1,7-Trimethyldecahydro-4H-cyclopropa[e]azulen-4-one 
• 6790-66-5 (-)-apoaromadendrone 
• 73809-82-2 (1S,3aR,8aS)-3a-methyl-7-methylidene-1-propan-2-yl-2,3,5,6,8,8a-hexahydro-1H-azulen-4-one 

Downstream Products

• 70000-15-6 4β,10β-aromadendranediol 
• 70051-38-6 4β,10α-aromadendranediol 
• 53526-64-0 β-Spathulen 

Relevant academic research and scientific papers

Biomimetic synthesis of (+)-ledene, (+)-viridiflorol, (-)-palustrol, (+)-spathulenol, and psiguadial A, C, and D via the platform terpene (+)-bicyclogermacrene

(+)-Bicyclogermacrene is a strained bicyclic and common sesquiterpene found in several essential oils. A short and good yielding synthesis of bicyclogermacrene proceeding in seven steps is reported. This terpene is used as key platform intermediate for a biomimetic access to several aromadendrene sesquiterpenoids, such as ledene, viridiflorol, palestrol, and spathulenol. Furthermore, bicyclogermacrene is shown to be the terpene component in the synthesis of the meroterpenoids psiguadial A, C, and D. Let nature be your guide! A concise synthesis of the terpene (+)-bicyclogermacrene enables its use as a platform for a fast access to a range of different terpenoids of the aromadendrene family and meroterpenoids of the psiguadial family (see scheme).

The synthesis of mono- and dihydroxy aromadendrane sesquiterpenes, starting from natural (+)-aromadendrene-III

The monoalcohols (-)-globulol (2), (-)-epiglobulol (3), (-)-ledol (4), and (+)-viridiflorol (5) were synthesized from (+)-aromadendrene (1). The cis-fused alloaromandedrone (14), the key intermediate used in the synthesis of 4 and 5, was obtained from the trans-fused apoaromadendrone (13) via a selective protonation of the thermodynamic enol trimethylsilylether 15. After hydroxylation of the tertiary C11 of 13 with RuO4, (+)-spathulenol (6), (-)-allospathulenol (7), and the aromadendrane diols 8-11 could be prepared. Compounds 2-11 were tested for antifungal properties, but their activity was only moderate.

FIRST PREPARATION OF (+)-SPATHULENOL. REGIO- AND STEREOSELECTIVE OXIDATION OF (+)-AROMADENDRENE WITH OZONE.

(+)-Spathulenol was prepared for the first time in three reaction steps from (+)-aromadendrene by two subsequent ozonizations the second of which was regio- and stereoselective, followed by a wittig reaction.The overall recycle yield was 13percent.

New Sesquiterpenoids from Clary Sage Oil (Salvia sclarea L.)

Six sesquiterpenoids, (2R,5E)-2,12-epoxycaryophyll-5-ene (1), (2R,5E)-caryophyll-5-en-12-al (2), (2S,5E)-caryophyll-5-en-12-al (3), isospathulenol (4), (1R,5R)-1,5-epoxysalvial-4(14)-ene (5), and salvial-4(14)-en-1-one (6) have been identified for the first time in clary sage oil (Salvia sclarea L.).The structures and absolute configurations of 1-6 are corroborated by partial syntheses and their organoleptic properties are discussed.The compounds 5, 6 and mintsulfide (14) possess the rare C-skeleton C, for which the semisystematic name 'salvialane' is proposed.The sesquiterpenoids 1-5 are new.