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Olivetol Basic information
Product Name: Olivetol
Synonyms: 5-PENTYLRESORCINOL;5-PENTYL 1,3-BENZENEDIOL;5-N-PENTYLRESORCINOL;5-AMYL RESORCINOL;3,5-dihydroxyamylbenzene;AURORA KA-7378;OLIVETOL;Olivetol（3,5-hydroxypentylbenzene）
CAS: 500-66-3
MF: C11H16O2
MW: 180.24
EINECS: 207-908-8
Product Categories: API intermediates;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;500-66-3
Mol File: 500-66-3.mol
Olivetol Structure
Olivetol Chemical Properties
Melting point 46-48 °C(lit.)
Boiling point 164 °C
density 1.068±0.06 g/cm3(Predicted)
Fp >230 °F
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Chloroform (Slightly), Methanol (Slightly)
form Solid
pka 9.59±0.10(Predicted)
color Colourless to Beige
Stability: Light Sensitive
InChI InChI=1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3
InChIKey IRMPFYJSHJGOPE-UHFFFAOYSA-N
SMILES C1(O)=CC(CCCCC)=CC(O)=C1
CAS DataBase Reference 500-66-3(CAS DataBase Reference)
NIST Chemistry Reference 1,3-Benzenediol, 5-pentyl-(500-66-3)
EPA Substance Registry System Olivetol (500-66-3)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/39
WGK Germany 3
RTECS VH2880000
HS Code 2907290090
MSDS Information
Provider Language
Olivetol English
SigmaAldrich English
Olivetol Usage And Synthesis
Chemical Properties Olivetol is an off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106°F). Olivetol is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 5 is replaced by a pentyl group. It has a role as a lichen metabolite.
Physical properties light purple to brown crystalline mass.
Uses Olivetol was used as a template molecule in the synthesis of molecularly imprinted polymer (MIP). It was also used as an inhibitor of (S)-mephenytoin 4'-hydroxylase activity of recombinant CYP2C19.
Application Olivetol is a precursor in various syntheses of tetrahydrocannabinol.
Preparation olivetol can also be formed through hydrolysis of intermediate polyketide CoAs or spontaneous cyclization.
synthesis of Olivetol
Definition ChEBI: Olivetol is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 5 is replaced by a pentyl group. It has a role as a lichen metabolite.
Synthesis Reference(s) The Journal of Organic Chemistry, 42, p. 3456, 1977 DOI: 10.1021/jo00441a036
General Description Olivetol appears as off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106°F). (NTP, 1992)
Air & Water Reactions Sensitive to air. Insoluble in water.
Reactivity Profile Olivetol is incompatible with acid chlorides, acid anhydrides and oxidizing agents.
Fire Hazard Olivetol is probably combustible.
Biological Activity Olivetol (5-Pentylresorcinol, 5-n-Amylresorcinol) is a naturally occurring organic compound being a precursor in various syntheses of tetrahydrocannabinol. It acts as a competitive inhibitor of the cannabinoid receptors CB1 and CB2.
Safety Olivetol is still a very new product. It has not been researched nearly enough to prove it's safe to use. So far, no one has reported any adverse side effects as far as we know. Until more information is available, carefully control your THC intake instead of relying on an untested gelcap.
Mode of action When you look at olivetol's molecular structure, it'll look very familiar. It's as if someone took a THC molecule and sliced it in two. Olivetol, like THC, works by binding with the CB1 receptors that exist all over your body and brain. But, olivetol is thought to be smaller and stickier than THC, so that helps it reduce a raging high in two ways. First, it slips into any open receptors before THC can get there to block them—so you won't get any higher. Second, it bumps into THC molecules that are already lodged in a CB1 receptor to knock them loose and take their place. That's how it brings you down.
According to numerous personal accounts, olivetol works, but we don't know exactly how it does so. More research and investigation is needed, but in theory it's very similar to how Narcan acts to reverse opiate overdoses.
Olivetol Preparation Products And Raw materials
Raw materials Acetic acid-->Sodium-->Government regulation-->Acetone-->Pyridine-->Diethyl malonate-->Sodium dithionite-->Hexanal-->3-Nonen-2-one-->Benzenemethanol, α-butyl-3,5-bis(phenylmethoxy)--->3,5-Bis(benzyloxy)benzoic acid benzyl ester-->methyl 6-n-pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate-->methyl 2,4-dihydroxy-6-pentylbenzoate-->3,5-Dibenzyloxybenzyl alcohol-->Olivetol Dimethyl Ether-->3,5-Dibenzyloxybenzaldehyde-->3,5-Dihydroxybenzoic acid-->3,5-DIMETHOXYBENZOYL CHLORIDE
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