5259-01-8

Basic information

• Product Name: grevillol
• Synonyms: grevillol;5-Tridecyl-1,3-benzenediol;Bilobol C13:0
• CAS NO: 5259-01-8
• Molecular Formula: C₁₉H₃₂O₂
• Molecular Weight: 292.46
• Mol File: 5259-01-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 426.2°C at 760 mmHg
• Flash Point: 187.6°C
• Appearance: /
• Density: 0.972g/cm³
• Vapor Pressure: 7.26E-08mmHg at 25°C
• Refractive Index: 1.514
• Storage Temp.: 2-8°C
• CAS DataBase Reference: grevillol(CAS DataBase Reference)
• NIST Chemistry Reference: grevillol(5259-01-8)
• EPA Substance Registry System: grevillol(5259-01-8)

Safety Data

• Hazard Codes: Xi
• Statements: 41-43
• Safety Statements: 26-36/37-39
• Hazardous Substances Data: 5259-01-8(Hazardous Substances Data)

Usage

Uses

5-Tridecylresorcinol and other resorcinol derivatives have been used to study the cytotoxic and antifungal apotential

InChI:InChI=1/C19H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-14-18(20)16-19(21)15-17/h14-16,20-21H,2-13H2,1H3

Upstream product

• 61621-63-4 2,4-Dihydroxy-6-tridecyl-benzoic acid ethyl ester 
• 5259-04-1 1,3-dimethoxy-5-tridecylbenzene 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 168697-62-9 1-(3,5-dimethoxyphenyl)-2-hydroxytridecane 
• 185249-83-6 3,5-dimethoxybenzyl trimethylsilyl ether 
• 185249-87-0 Methanesulfonic acid 1-(3,5-dimethoxy-benzyl)-dodecyl ester 
• 500-99-2 3,5-dimethoxyphenol 
• 60319-09-7 3,5-dimethoxyphenyl trifluoromethanesulfonate 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 143-15-7 1-dodecylbromide 
• 171569-31-6 1,3-dimethoxy-5-(tridec-1-enyl)benzene 
• 15890-72-9 laurylmagnesium bromide 
• 61621-62-3 3,5-Dibromo-2,4-dihydroxy-6-tridecyl-benzoic acid ethyl ester 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 

Downstream Products

• 5259-04-1 1,3-dimethoxy-5-tridecylbenzene 
• 5259-02-9 1,3-Diacetoxy-5-tridecyl-benzol 

Relevant articles and documents

Mapping the Mechanism of the Resorcinol Ring Formation Catalyzed by ArsB, a Type III Polyketide Synthase from Azotobacter vinelandii

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Concise access to primin, miconidin and related natural resorcinols

An efficient and short synthetic procedures affording the biologically active natural products primin, miconidin, olivetol, grevillol, and cardol (adipostatin A) in high yields are reported. The two strategies involve Sonogashira and Suzuki cross-couplings as the crucial steps for the installation of the alkyl side-chains. Syntheses start from cheap, commercially available 1-bromo-3,5-dimethoxybenezene to obtain 1,3-dimethoxy-5-(alk-1-yn-1-yl)benzene as the key intermediate. This intermediate can be easily and economically oxidized to provide primin in excellent overall yield while avoiding undesired side products by the virtue of its symmetry. The demethylation of the key intermediate affords natural resorcinols olivetol, grevillol, and cardol, respectively. The reduction of primin provides its hydroquinone derivative miconidin.

Alkylresorcylic acid synthesis by type III polyketide synthases from rice Oryza sativa

Alkylresorcinols, produced by various plants, bacteria, and fungi, are bioactive compounds possessing beneficial activities for human health, such as anti-cancer activity. In rice, they accumulate in seedlings, contributing to protection against fungi. Alkylresorcylic acids, which are carboxylated forms of alkylresorcinols, are unstable compounds and decarboxylate readily to yield alkylresorcinols. Genome mining of the rice Oryza sativa identified two type III polyketide synthases, named ARAS1 (alkylresorcylic acid synthase) and ARAS2, that catalyze the formation of alkylresorcylic acids. Both enzymes condensed fatty acyl-CoAs with three C2 units from malonyl-CoA and cyclized the resulting tetraketide intermediates via intramolecular C-2 to C-7 aldol condensation. The alkylresorcylic acids thus produced were released from the enzyme and decarboxylated non-enzymatically to yield alkylresorcinols. This is the first report on a plant type III polyketide synthase that produces tetraketide alkylresorcylic acids as major products.