30359-01-4

Basic information

• Product Name: Centrolobol
• Synonyms: (R)-(-)-1,7-Bis(p-hydroxyphenyl)-3-heptanol;Centrolobol
• CAS NO: 30359-01-4
• Molecular Formula: C₁₉H₂₄O₃
• Molecular Weight: 300.39206
• Mol File: 30359-01-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Centrolobol(CAS DataBase Reference)
• NIST Chemistry Reference: Centrolobol(30359-01-4)
• EPA Substance Registry System: Centrolobol(30359-01-4)

Safety Data

• Hazardous Substances Data: 30359-01-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Centrolobol is used as a medicinal compound for its anti-inflammatory properties, helping to reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Oncology:
Centrolobol is used as an anti-tumor agent, exhibiting potential in the treatment of cancer by inhibiting tumor growth and progression. Its anti-cancer effects are currently under investigation for possible applications in oncology.
Used in Antifungal Applications:
Centrolobol is used as an anti-fungal agent, showing promise in combating fungal infections due to its anti-fungal activity. This property makes it a potential candidate for the development of new antifungal drugs.

Upstream product

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• 104109-45-7 (3R)-1,7-Bis-(4-hydroxyphenyl)-3-heptanol 3-O-β-D-glucopyranoside 
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Downstream Products

• 130233-83-9 1,7-bis(4'-hydroxyphenyl)-3-heptanone 

Relevant articles and documents

Absolute Configuration of Platyphylloside and (-)-Centrolobol

The ansolute configuration of platyphylloside was established to be S by 13C NMR spectroscopy.On the basis of this establishment, the S-configuration previously assigned to the chirality at C-3 of (-)-centrolobol was revised to the R-configuration.

Studies on the constituents of aceraceae plants. XII. Two new diarylheptanoid glycosides from Acer triflorum

Two new diarylheptanoid glycosides, named aceroside XII (7), C30H42O12, [α](D) -70.3°, and aceroside XIII (8), C25H34O8, [α](D) -40.2°, were isolated along with triterpenoids and caffeoyl esters from the branches of Acer triflorum KOM. (Aceraceae). On acid hydrolysis, 7 yielded (-)-centrolobol (9), glucose and apiose. On partial hydrolysis, 7 gave 8 and apiose. Acerosides XII (7) and XIII (8) were determined to be the 4''-O-β-D-apiofuranosyl-(1 → 6)-β-D-glucopyranoside and the 4-O-β-D-glucopyranoside of (-)-centrolobol, respectively, on the basis of chemical and spectral evidence.

Identification of centrolobol as the platyphylloside metabolite responsible for the observed effect on in vitro digestibility of hay

Syntheses of the metabolites from platyphylloside, a phenol causing digestibility inhibition in rumen fluid, have been performed to identify the active metabolite. 1,7-Bis(4′-hydroxyphenyl)-3-heptanone (3-platyphyllone), racemic, and the two enantiomers o

Studies on the Constituents of Aceraceae Plants. VI. Revised Stereochemistry of (-)-Centrolobol, and New Glycosides from Acer nikoense

Two diarylheptanoid glycosides, named aceroside VII (8), C25H34O8, mp 144-145 deg C, 15D -28.4 deg, and aceroside VIII (9), C30H42O12, 15D -64.8 deg were isolated from the stem bark of Acer nikoense MAXIM (Aceraceae).On acid hydrolysis 8 yielded (-)-centrolobol (10) and glucose, while 9, on partial hydrolysis, gave 8 and apiose.Acerosides VII (8) and VIII (9) were determined to be the 3-O-β-D-glucopyranoside and the 3-O-β-apiofuranosyl-(1->6)-β-D-glucopyranoside of (-)-centrolobol (10), respectively, on the basis of carbon-13 nuclear magnetic resonance (13C-NMR) spectral analyses and additional chemical data.The absolute configuration S for (-)-centrolobol (10) has been claimed, but the authors propose its revision to R(-) on the basis of Brewster's empirical rule on the correlation between absolute configuration and optical rotation.The stereochemistries of some compounds related to 10 such as acerogenin A (1) and (-)-centrolobin should also be revised.At the same time, partial revision of the 13C-NMR signal assignments for acerosides III (3) and VI (4) is also necessary.Keywords - Acer nikoense; diarylheptanoid; R(-)-centrolobol; aceroside (VII, VIII); Brewster empirical rule; absolute configuration revision