105368-62-5

Basic information

• Product Name: GUGGULTETROL-18,1,2,3,4-OCTADECANETETROL
• Synonyms: GUGGULTETROL-18,1,2,3,4-OCTADECANETETROL
• CAS NO: 105368-62-5
• Molecular Formula: C18H38 O4
• Molecular Weight: 318.49
• Mol File: 105368-62-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: GUGGULTETROL-18,1,2,3,4-OCTADECANETETROL(CAS DataBase Reference)
• NIST Chemistry Reference: GUGGULTETROL-18,1,2,3,4-OCTADECANETETROL(105368-62-5)
• EPA Substance Registry System: GUGGULTETROL-18,1,2,3,4-OCTADECANETETROL(105368-62-5)

Safety Data

• Hazardous Substances Data: 105368-62-5(Hazardous Substances Data)

Upstream product

• 517920-38-6 C₂₁H₄₂O₄ 
• 105265-49-4 5,6,7,8,9,10,11,12,13,14,15,16,17,18,-tetradecadeoxy-D-xylo-octadecofuranose 
• 1233497-23-8 (2S,3R,4R)-4-(methoxymethoxy)octadecane-1,2,3-triol 
• 929540-05-6 (R)-1-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pentadecan-1-ol 

Relevant articles and documents

Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells

A cycloartane-type triterpenoid (1), an aliphatic alcohol glycoside (2), an eudesmane-type sesquiterpenoid (3), and a guaiane-type sesquiterpenoid (4) were isolated from the resinous exudates of Commiphora opobalsamum along with six known sesquiterpenoids (5-10). Their structures were established by extensive analysis of their 1D and 2D NMR spectroscopic data and chemical methods. The isolated compounds 1-3 and 5-9 were tested against human prostate cancer cell PC 3 and LNCaP. Among them, 1 and 2 showed moderate antiproliferative effects on human prostate cancer cell lines with IC50 values ranging from 5.7 to 23.6 μM; they were also able to inhibit the expression of androgen receptor (AR) in LNCaP cells. The six sesquiterpenoids were inactive in the bioassays.

A short enantioselective synthesis of guggultetrol, a naturally occurring lipid

An enantioselective synthesis of the naturally occurring lipid, guggultetrol, is described with an overall yield of 24% starting from commercially available l-pentadecanol in ten linear steps. The key chiral-inducing steps include a Sharpless asymmetric epoxidation of allylic alcohol and a dihydroxylation of an α,β-unsaturated ester.

SYNTHESIS AND PROPERTIES OF SOME STEREOISOMERIC LONG-CHAIN 1,2,3,4-TETROLS

Syntheses of 1,2S,3R,4R, 1,2S,3R,4S, 1,2R,3S,4R, and 1,2S,3S,4R-icosanetetrol, as well as of 1,2S,3S,4R-octadecanetetrol, are described, all based upon Wittig reactions of 1,2,3-protected pentodialdo-1,4-furanoses, serving as "chiral templates", with pentadecyl (or tridecyl) triphenylphosphorane, followed by catalytic hydrogenation, hydrolysis, and reduction.The tetrols, all forming liquid crystals on heating, are characterized spectroscopically and as their O-tetraacetates.The latter serve admirably for GLC-separation and -characterization of all non-enantiomeric tetrols.From the sign of rotation and GLC-comparison with the synthetic O-tetraacetates it follows that the 1,2,3,4-octadecanetetrol and 1,2,3,4-icosanetetrol, reported several years ago as the predominant members of a homologous series of tetrols derived from the gum-resin of Commiphora mukul, possess the 2S,3S,4R-configuration ("D-xylo").