58016-28-7 Usage
Description
Methyl 2,4-dihydroxy-6-pentylbenzoate, also known as Methyl Olivetolate, is an organic compound derived from the olivetol family. It is characterized by its chemical structure, which includes a benzoate backbone with hydroxyl groups at the 2 and 4 positions, and a pentyl chain attached at the 6 position. methyl 2,4-dihydroxy-6-pentylbenzoate has been identified for its potential applications in various fields, particularly in the pharmaceutical and chemical industries.
Uses
Used in Pharmaceutical Industry:
Methyl 2,4-dihydroxy-6-pentylbenzoate is used as an intermediate in the synthesis of Δ9-Tetrahydrocannabinolic Acid (THCA), a compound with potential therapeutic applications. It plays a crucial role in the production of Acid A & B (T293235), which are derivatives of THCA.
Used in Drug Testing:
Methyl Olivetolate is utilized as one of the substances screened for in meconium drug testing. This testing is performed to detect the presence of medicinal opioids among addicted mothers, helping to identify potential cases of neonatal opioid withdrawal syndrome and ensure appropriate medical intervention for the newborn.
Used in Neuroprotection:
Δ9-Tetrahydrocannabinolic Acid, synthesized using Methyl Olivetolate, has been shown to protect dopaminergic neurons against 1-methyl-4-Phenylpyridinium (MPP+) induced cell death. This suggests that Methyl Olivetolate, through its role in THCA synthesis, may contribute to the development of treatments for neurodegenerative diseases, such as Parkinson's disease, where dopaminergic neuron loss is a significant factor.
Synthesis Reference(s)
Tetrahedron Letters, 23, p. 2935, 1982 DOI: 10.1016/S0040-4039(00)87498-5
Check Digit Verification of cas no
The CAS Registry Mumber 58016-28-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,0,1 and 6 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 58016-28:
(7*5)+(6*8)+(5*0)+(4*1)+(3*6)+(2*2)+(1*8)=117
117 % 10 = 7
So 58016-28-7 is a valid CAS Registry Number.
58016-28-7Relevant articles and documents
SYNTHESIS OF PHYTOCANNABINOIDS INCLUDING A DECARBOXYLATION STEP
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Page/Page column 16, (2019/03/05)
method for decarboxylating a carboxylated phytocannabinoid compound of Formula I to form a phytocannabinoid compound of Formula II: Formula I Formula II wherein: R1 is selected from the group consisting of: substituted or unsubstituted C1-C5 alkyl; R2 is selected from the group consisting of: OH or O, and R3 is selected from the group consisting of: a substituted or unsubstituted cyclohexene, a substituted or unsubstituted C2-C8 alkene, or a substituted or unsubstituted C2-C8 dialkene; or R2 is O, and R2 and R3 together form a ring structure in which R2 is an internal ring atom; wherein the method includes heating a reaction mixture comprising the carboxylated phytocannabinoid compound and a polar aprotic solvent in the presence of a LiCl for a time sufficient to decarboxylate at least a portion of the carboxylated phytocannabinoid compounds and form the phytocannabinoid compound.
Chemistry of 1,3,5-Tris(trimethylsiloxy)-1-methoxyhexa-1,3,5-triene, a β-Tricarbonyl Trianion Equivalent
Chan, T. H.,Stoessel, D.
, p. 2423 - 2428 (2007/10/02)
The title compound has been synthesized and its chemistry studied.Condensation with orthoesters, acid chlorides, or imidazolides gave aromatic compounds in a 5C + 1C condensation.A formal synthesis of lasiodiplodin has been completed.
Convenient Syntheses of Alkyl β-Resorcylate Derivatives
Barrett, Anthony G. M.,Morris, Timothy M.,Barton, Derek H. R.
, p. 2272 - 2277 (2007/10/02)
Syntheses of methyl 2,4-dihydroxy-6-methyl- (1a) and -3,6-dimethylbenzoates (1b) and methyl 2,4-dihydroxy-6-pentylbenzoate (1c) are described.Condensation reactions of dimethyl sodiomalonate with the dianion derived from pentane-2,4-dione or the dimerisation of the methyl acetoacetate dianion or the acetylation of the trianion derived from methyl 3,5,7-trioxo-octanoate gave (1a) (78percent) after work-up at pH 9.Analogous convenient, short, optimised syntheses of (1b and c) are given in detail.