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Olivetol CAS 500-66-3

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Olivetol Supplement

Basic Info of Olivetol

What is Olivetol?

Olivetol, also known as 5-pentyl resorcinol or 5-pentyl-1,3-benzodiol, is an organic compound present in some lichen species and can be easily extracted. 3,5-Dihydroxypentylbenzene is an important pharmaceutical intermediate , which was first obtained by degrading lichenic acid (also known as D-sunroic acid, pentyl icylic acid) extracted from lichen plants. It is also a precursor for the synthesis of tetrahydrocannabinol.

3,5-Dihydroxyalkylbenzene has a variety of biological activities, and has killing effect on fungi and bacteria of various pathogens. In recent years, it has been found that in the presence of copper chloride and oxygen, high concentrations of 3,5-dihydroxyalkylbenzene can fragment DNA. Therefore, it is used for inhibiting and treating human immunodeficiency, cancer and other malignant tumors caused by retrovirus, and the effect is remarkable. 3,5-dihydroxyalkylbenzene can also be used to synthesize cannabinoids. Cannabinoids are a general term for a class of substances with similar chemical structures related to the physiological activity of the human body in cannabis. Analgesic, calming, anti-inflammatory, digestive and antihypertensive. The generation in this class of compounds is 3,5-dihydroxypentylbenzene (Olivetol),

Olivetol Uses

  1. Olivetol is an important pharmaceutical intermediate. It was first obtained by degrading lichenic acid (also known as D-sunroic acid, pentyl-caprylic acid) extracted from lichen plants. It is mainly used for laboratory research and development and chemical production. in the process.
  2. Olivetol is a precursor for THC-related synthesis.
  3. Olivetol is also produced by many insects as a pheromone, insect repellent or preservative.
  4. Olivetol is used in various ways to produce synthetic analogues of THC. The related substance olive acid (OLA) is produced in cannabis plants, which may be involved in the biosynthesis of tetrahydrocannabinol (THC).
  5. Olivetol is used as a template molecule in the synthesis of molecularly imprinted polymers (MIPs). It is also used as an inhibitor of (s) – mephenytoin 4 ‘- hydroxylase activity of recombinant CYP2C19.

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Application of Olivetol

CN201611230150.7 discloses a method for synthesizing cannabidiol compounds. The steps are that 3,5-dihydroxypentylbenzene is used as a starting material, phenolic hydroxybenzyl is protected, 2-pyridinesulfonyl is protected, and palladium acetate is used as a catalyst , Oxygen as oxidant, direct coupling of two aryl carbon-hydrogen bonds to synthesize 6H-benzo[c]chromene compounds in one step, and then through oxidation, deprotection, methylation, and high yield synthesis of cannabidiol.

The method of the invention realizes the efficient and concise synthesis of cannabidiol through the activation of -C-H-bond and direct oxidative aryl coupling as a key step in synthesizing cannabidiol. Compared with the traditional method, the method has the advantages of simple operation, higher reaction yield, environmental friendliness and high atom utilization rate.

Preparation of Olivetol

Add 156g benzene, 900mL dichloromethane and 146.5g anhydrous aluminum trichloride into a 2L three-necked flask, cool down to 0-5°C, slowly add 120.5g n-valeryl chloride dropwise, keep the internal temperature 0-10 °C. After the dropwise addition, the temperature was raised to 40 °C, and the reaction was stirred for 2 h.

Under ice bath cooling, 500 mL of 1N hydrochloric acid solution was slowly added dropwise, and the solution was separated after the dropwise addition was completed. The aqueous phase was extracted with an additional 400 mL of DCM. After combining the organic phases, concentrate under reduced pressure and distill to obtain 142 g of valerophenone with a yield of 87%.

In a 1L three-necked flask, 200mL of fuming nitric acid and 200mL of 5% sulfuric acid were mixed within 20°C to form a mixed acid, then cooled to within 10°C, and 129.6g of valerophenone was slowly added dropwise. The dropwise addition process controlled the internal temperature to 0-10°C. After the dropwise addition was completed, the temperature was raised to 50° C. for 2 hours, and the reaction was continued for 5 hours.

After cooling to 20°C, the reaction solution was poured into crushed ice, a solid was precipitated, filtered, the filter cake was dissolved in DCM, and the liquid was separated, and the organic phase was concentrated again to obtain a crude product. The crude product was mixed with PE and EA to dissolve the crystals and dried to obtain 156.5 g of 3,5-dinitrovalerophenone, with a yield of 78% and a purity of 98.3%.

Reference

  1. Olivetol – WikiPedia
  2. The Pherobase (Database of pheromones and semiochemicals). 5-Pentylresorcinol. Retrieved 18 January 2014
  3. [Chinese invention] CN201210511883.3 A kind of synthetic method of alkyl-protected 3,5-dihydroxyalkylbenzene
  4. [China Invention, China Invention Authorization] CN201611230150.7 A synthetic method of cannabidiol compounds
  5. Hassuni, I; Razxouk, H (2005). “Olivetol: Constituent of lichen Evernia prunastri Ach. or “oakmoss””Physical and Chemical News26: 98–103.

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