Purity:99%
|
491-72-5 Name |
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|
Name |
Olivetolic acid |
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Synonym |
olivetolic acid;2,4-Dihydroxy-6-pentylbenzoic acid;Olivetolcarboxylic acid;139400;olivanic acid powder 98%;Benzoic acid, 2,4-dihydroxy-6-pentyl- |
|
491-72-5 Chemical & Physical Properties |
|
|
Melting point |
143 °C |
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Boiling point |
403.9ºC at 760 mmHg |
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Density |
1.237g/cm3 |
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Molecular Formula |
C12H16O4 |
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Molecular Weight |
224.25300 |
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Flash Point |
212.2ºC |
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PSA |
77.76000 |
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LogP |
2.52870 |
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Exact Mass |
224.10500 |
|
Vapour Pressure |
3.01E-07mmHg at 25°C |
|
Index of Refraction |
1.581 |
Olivetolic acid (OLA) is a precursor in the synthesis of primin and tetrahydrocannabinol, it is a member of the class of benzoic acids. Olivetolic acid (OLA) is a plant secondary metabolite sourced from PKS III catalysis, which along with its prenylated derivatives has various pharmacological activities.
Definition
ChEBI: A member of the class of benzoic acids that is salicylic acid in which the hydrogens ortho- and para- to the carboxy group are replaced by a pentyl and a hydroxy group, respectively.
InChI:InChI=1/C12H16O4/c1-2-3-4-5-8-6-9(13)7-10(14)11(8)12(15)16/h6-7,13-14H,2-5H2,1H3,(H,15,16)
Olivetolic acid is anticonvulsant against hyperthermia-induced seizures in Scn1a +/- mice. The structurally related CBGA methyl ester compound was ineffective. Future studies could examine whether the anticonvulsant activity of olivetolic acid extends to other animal models of epilepsy.
Here, we aimed to develop a bioprocess for the production of olivetolic acid, the main precursor of cannabinoids synthesized by a recently engineered D. discoideum strain. We developed a robust and reliable scale-up strategy for amoeba-based bioprocesses and evaluated its applicability for the production of the cannabinoid precursor olivetolic acid.
Olivetolic acid displayed modest anticonvulsant activity against hyperthermia-induced seizures in the Scn1a+/ mouse model of Dravet syndrome despite poor brain penetration. The efect was, however, comparable to the known anticonvulsant cannabinoid cannabidiol in this model. Future studies could explore the anticonvulsant mechanism(s) of action of olivetolic acid and examine whether its anticonvulsant efect extends to other seizure types
2,4-dihydroxyl-6-pentylbenzaldehyde
2,4-dihydroxyl-6-pentylbenzoic acid
| Conditions | Yield |
|---|---|
|
With sodium chlorite; sodium dihydrogen phosphate monohydrate; In water; dimethyl sulfoxide; at 20 ℃; Inert atmosphere;
|
78% |
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With sodium chlorite; sodium dihydrogen phosphate monohydrate; In water; dimethyl sulfoxide; at 20 ℃; for 12h; Inert atmosphere;
|
78% |
|
With sodium chlorite; sodium dihydrogenphosphate; In water; dimethyl sulfoxide; at 0 - 20 ℃; for 14h;
|
50% |
|
Multi-step reaction with 2 steps
1: acetone; pyridine / Erwaermen des Reaktionsprodukts mit Kaliumpermanganat in wss. Aceton
2: aqueous ammonia
With pyridine; ammonium hydroxide; acetone;
|
|
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Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 12 h / Reflux
2: sodium dihydrogenphosphate; sodium chlorite / dimethyl sulfoxide; water / 14 h / 20 °C
3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / 750.08 Torr
With sodium chlorite; sodium dihydrogenphosphate; palladium 10% on activated carbon; hydrogen; potassium carbonate; In water; dimethyl sulfoxide; ethyl acetate; acetone;
|
2,4-bis(benzyloxy)-6-pentylbenzoic acid
2,4-dihydroxyl-6-pentylbenzoic acid
| Conditions | Yield |
|---|---|
|
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 24h; under 750.075 Torr;
|
97% |
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With palladium on activated charcoal; hydrogen; In ethyl acetate; for 18h;
|
88% |
ethanol
olivetoric acid
semicarbazide acetate
anziaic acid
methyl 2,6-dihydroxy-6-pentylbenzoate
2,4-dimethoxy-6-pentylbenzoic acid methyl ester
anziaic acid
benzyl 2,4-dihydroxy-6-pentylbenzoate
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