22976-40-5

Basic information

• Product Name: Olivetol Dimethyl Ether
• Synonyms: Olivetol Dimethyl Ether;1,3-DiMethoxy-5-pentylbenzene;1,3-DiMethoxy-5-pentyl-benzene;3,5-DiMethoxyaMylbenzene;5-Pentylresorcinol DiMethyl Ether;Di-O-Methylolivetol
• CAS NO: 22976-40-5
• Molecular Formula: C₁₃H₂₀O₂
• Molecular Weight: 208.2967
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 22976-40-5.mol

Chemical Properties

• Boiling Point: 130 °C
• Appearance: /
• Density: 0.978 g/cm3(Temp: 25 °C)
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: Olivetol Dimethyl Ether(CAS DataBase Reference)
• NIST Chemistry Reference: Olivetol Dimethyl Ether(22976-40-5)
• EPA Substance Registry System: Olivetol Dimethyl Ether(22976-40-5)

Safety Data

• Hazardous Substances Data: 22976-40-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Olivetol Dimethyl Ether is used as an intermediate for the synthesis of tetrahydrocannabinol (THC) due to its role in the production process of Olivetol Dimethyl Ether. This application is significant in the development of medications and therapies that utilize the properties of THC for various medical conditions.

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 2079, 1976 DOI: 10.1016/S0040-4039(00)93823-1

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 71-43-2 benzene 
• 693-03-8 n-butyl magnesium bromide 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 24406-16-4 lithium di-n-butylcuprate 
• 165395-21-1 3,5-dimethoxybenzyl toluene-p-sulfonate 
• 185249-86-9 Methanesulfonic acid 1-(3,5-dimethoxy-benzyl)-butyl ester 
• 109-72-8 n-butyllithium 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 64-17-5 ethanol 
• 114085-80-2 1-(3,4,5-trimethoxyphenyl)pentan-1-one 
• 17213-58-0 3,5-dimethoxybenzamide 
• 212757-44-3 (4R,5R)-4-(3,5-dimethoxyphenyl)-5-propyl-1,3-dioxolane-2-thione 
• 212757-55-6 (4S,5S)-4-(3,5-dimethoxyphenyl)-5-propyl-1,3-dioxolane-2-thione 

Downstream Products

• 15121-94-5 primine 
• 3410-84-2 2,6-dimethoxy-4-pentylbenzaldehyde 
• 112639-04-0 2,4-dibromo-1,5-dimethoxy-3-pentylbenzene 
• 500-66-3 Olivetol 
• 139552-96-8 resorstatin [2-hexyl-5-pentylbenzene-1,3-diol] 
• 6087-61-2 (+)-trans-Δ⁸-tetrahydrocannabinol 
• 79994-21-1 condidymic acid 
• 63171-67-5 1,5-dimethoxy-3-pentylcyclohexa-1,4-diene 
• 1004305-27-4 2,6-dimethoxy-4-pentylbenzeneboronic acid 
• 34272-58-7 2-methoxy-6-pentyl-1,4-hydroquinone 
• 20408-52-0 6-carboxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromen-5-ol 
• 20675-51-8 cannabichromene 
• 930597-99-2 1-(2,6-dimethoxy-4-pentylphenyl)prop-2-en-1-ol 
• 154395-99-0 3-[2,6-Dimethoxy-4-pentylphenyl]cyclohexanone 

Relevant articles and documents

On the deprotonation of η6-1,3-dimethoxybenzene-Cr(CO)3 derivatives: Influence of the reaction conditions on the regioselectivity

The regioselectivity of deprotonation/alkylation reactions of η6-1,3-dimethoxybenzene-Cr(CO)3 (5), η6-1,3-dimethoxy-5-methylbenzene-Cr(CO)3 (6) and 2-substituted derivatives of these compounds was investigated.

CANNABINOID DERIVATIVES

This disclosure relates to cannabinoid derivatives of formula (I), pharmaceutical compositions comprising them, and methods of using the cannabinoid derivatives in treating or preventing a diseases associated with a cannabinoid receptor in a subject in ne

CANNABIGEROL DERIVATIVES AND USE THEREOF AS CANNABINOID RECEPTOR MODULATORS

The synthesis of a range of pentylbezene- 1,3-diol compounds of formula I is disclosed. These compounds bind to cannabinoid 1 and 2 receptors (CB1 and CB2), and are thus presumed to be useful in modulating the activity of such receptors. Accordingly, the

Preparation method of 3,5-dihydroxyamylbenzene

The invention provides a preparation method of 3,5-dihydroxyamylbenzene. The preparation method comprises the following steps: with a 3,5-dialkoxy benzoate compound as a raw material, subjecting the 3,5-dialkoxy benzoate compound to reacting with valeronitrile to generate a beta-ketone nitrile compound, hydrolyzing a cyano group to generate a carboxylic acid compound, performing a decarboxylation reaction to obtain 3,5-dialkoxyphenylpentanone, performing Huang Ming-long reaction or catalytic hydrogenation to convert 3,5-dialkoxyphenylpentanone into 3,5-dialkoxyamylbenzene, and finally, reducing an alkoxy group into a phenolic hydroxyl group so as to obtain 3,5-dihydroxyamylbenzene. The preparation method provided by the invention overcomes the defects of high cost, complex route, low yield, poor purity and the like of traditional processes.

Design of Negative and Positive Allosteric Modulators of the Cannabinoid CB2Receptor Derived from the Natural Product Cannabidiol

Cannabidiol (CBD), the second most abundant of the active compounds found in the Cannabis sativa plant, is of increasing interest because it is approved for human use and is neither euphorizing nor addictive. Here, we design and synthesize novel compounds taking into account that CBD is both a partial agonist, when it binds to the orthosteric site, and a negative allosteric modulator, when it binds to the allosteric site of the cannabinoid CB2 receptor. Molecular dynamic simulations and site-directed mutagenesis studies have identified the allosteric site near the receptor entrance. This knowledge has permitted to perform structure-guided design of negative and positive allosteric modulators of the CB2 receptor with potential therapeutic utility.

Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core

Based on the significant anti-inflammatory activity of natural quinone primin (5a), series of 1,4-benzoquinones, hydroquinones, and related resorcinols were designed, synthesized, characterized and tested for their ability to inhibit the activity of cyclooxygenase (COX-1 and COX-2) and 5-lipoxygenase (5-LOX) enzymes. Structural modifications resulted in the identification of two compounds 5b (2-methoxy-6-undecyl-1,4-benzoquinone) and 6b (2-methoxy-6-undecyl-1,4-hydroquinone) as potent dual COX/5-LOX inhibitors. The IC50 values evaluated in vitro using enzymatic assay were for compound 5b IC50 = 1.07, 0.57, and 0.34 μM and for compound 6b IC50 = 1.07, 0.55, and 0.28 μM for COX-1, COX-2, and 5-LOX enzyme, respectively. In addition, compound 6d was identified as the most potent 5-LOX inhibitor (IC50 = 0.14 μM; reference inhibitor zileuton IC50 = 0.66 μM) from the tested compounds while its inhibitory potential against COX enzymes (IC50 = 2.65 and 2.71 μM for COX-1 and COX-2, respectively) was comparable with the reference inhibitor ibuprofen (IC50 = 4.50 and 2.46 μM, respectively). The most important structural modification leading to increased inhibitory activity towards both COXs and 5-LOX was the elongation of alkyl chain in position 6 from 5 to 11 carbons. Moreover, the monoacetylation in ortho position of bromo-hydroquinone 13 led to the discovery of potent (IC50 = 0.17 μM) 5-LOX inhibitor 17 (2-bromo-6-methoxy-1,4-benzoquinone) while bromination stabilized the hydroquinone form. Docking analysis revealed the interaction of compounds with Tyr355 and Arg120 in the catalytic site of COX enzymes, while the hydrophobic parts of the molecules filled the hydrophobic substrate channel leading up to Tyr385. In the allosteric catalytic site of 5-LOX, compounds bound to Tyr142 and formed aromatic interactions with Arg138. Taken together, we identified optimal alkyl chain length for dual COX/5-LOX inhibition and investigated other structural modifications influencing COX and 5-LOX inhibitory activity.

Synthesis method of 3, 5-dihydroxypentene benzene

The invention provides a synthesis method of 3, 5-dihydroxypentene benzene. The synthesis method comprises the following steps: reacting 3, 5-dimethoxyphenol used as a raw material with a sulfonate halide reagent to generate sulfonate, carrying out cross-coupling reaction with a nucleophilic reagent to introduce amyl, and finally reducing methoxyl into phenolic hydroxyl, thereby obtaining the product 3, 5-dihydroxypentene benzene. The synthesis method solves the defects of high cost, complex route, low yield, poor purity and the like of the traditional process.

METHODS FOR SYNTHESIS OF CANNABINOID COMPOUNDS

The present invention provides simple synthetic routes for the preparation of cannabinoid compounds such as CBD, CBDV, THC, THCV, CBN, HU-308, CBG, CBC, and derivatives thereof, which are stereoselective and provide the desired cannabinoid compound in high yield.

METHOD FOR THE METAL-FREE PREPARATION OF A BIARYL BY A PHOTOSPLICING REACTION AND THEIR USES

The present invention relates to a method for the metal-free preparation of a biaryl compound by a photosplicing reaction and its use in the preparation of chemical compounds, preferably of active ingredients e.g. in the fields of pharmaceuticals and agrochemicals. In particular, it refers to a method for the regiocontrolled preparation of a biaryl compound of formula (I): Ar-Ar' by photochemically reacting a precursor compound of formula (II): Ar-L-Ar' to form a biaryl compound of general formula: Ar-L-Ar' (II) → Ar-Ar' (I) wherein Ar and Ar', independently of each other, represent an unsubstituted or substituted C6-C20 aryl group or a heteroaryl group with 5–20 ring atoms selected from carbon, nitrogen, oxygen and sulfur, and L represents a group –X–Y–Z– as defined herein. The biaryl compounds are generally suitable as intermediates or key building blocks in a very broad spectrum of organic chemical syntheses and their respective utilities. Their use within the field of synthesis of active ingredients is an aspect of the invention, and their use in the preparation of pharmaceutically active ingredients is particularly preferred.

SYNTHESIS OF CANNABINOIDS

Provided are synthesis processes and intermediates for preparing cannabinoids and analogs.