491-72-5

Basic information

• Product Name: olivetolic acid
• Synonyms: olivetolic acid;2,4-Dihydroxy-6-pentylbenzoic acid;Olivetolcarboxylic acid
• CAS NO: 491-72-5
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.26
• Mol File: 491-72-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 143 °C
• Boiling Point: 403.9°Cat760mmHg
• Flash Point: 212.2°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 3.01E-07mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.41±0.34(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: olivetolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: olivetolic acid(491-72-5)
• EPA Substance Registry System: olivetolic acid(491-72-5)

Safety Data

• Hazardous Substances Data: 491-72-5(Hazardous Substances Data)

Usage

Uses

Olivetolic Acid is a precursor in the synthesis of primin and tetrahydrocannabinol.

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)

Synthetic route

2,4-bis(benzyloxy)-6-pentylbenzoic acid (104307-50-8) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 750.075 Torr; for 24h;	97%
With palladium on activated charcoal; hydrogen In ethyl acetate for 18h;	88%

2,4-dihydroxy-6-pentylbenzaldehyde (855875-40-0) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With sodium chlorite; sodium dihydrogen phosphate monohydrate In water; dimethyl sulfoxide at 20℃; 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 View Scheme
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 View Scheme

2,4-dihydroxy-3,5-dibromo-6-pentylbenzoic acid (86791-41-5) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With hydrogen; sodium hydrogencarbonate; palladium on activated charcoal Ambient temperature;	71%

ethanol (64-17-5) + olivetoric acid (491-47-4) + semicarbazide acetate (56542-16-6) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) + (6,8-dihydroxy-1-oxo-3-pentyl-1H-[2]isoquinolyl)-urea

anziaic acid (641-68-9) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With sulfuric acid anschliessend Behandeln mit Wasser;
With potassium hydroxide

2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid (529-47-5) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With potassium hydroxide

olivetoric acid (491-47-4) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With sulfuric acid anschliessend Behandeln mit Wasser;

glomelliferic acid (552-49-8) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With potassium hydroxide

2,4-bis-ethoxycarbonyloxy-6-pentyl-benzoic acid → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With ammonium hydroxide

3,5,7-Trioxo-dodecansaeure (7028-38-8) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With sodium acetate In ethanol

2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid (529-47-5) + tert-butyl alcohol (75-65-0) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) + tert-butyl 4-O-methylolivetolcarboxylate

Conditions	Yield
for 40h; Heating;

6-hydroxy-4-<4.6-dihydroxy-2-(2-oxo-heptyl-benzoyloxy>-2-pentyl-benzoic acid → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With ethanol; semicarbazide hydrochloride; sodium acetate

2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid (529-47-5) + methanol. KOH-solution → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

glomelliferic acid (552-49-8) + aqueous KOH-solution → 8-hydroxy-6-methoxy-3-propylisocoumarin (52589-15-8) + 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

3,5-dibromo-2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester (58497-40-8) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / conc. H2SO4 / 1 h / Ambient temperature 2: 71 percent / NaHCO3, H2 / Pd-C (10percent) / Ambient temperature View Scheme

Olivetol (500-66-3) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate / 18 h / 0 - 20 °C 2: sodium dihydrogenphosphate; sodium chlorite / dimethyl sulfoxide; water / 14 h / 0 - 20 °C View Scheme
Multi-step reaction with 4 steps 1: trichlorophosphate / 18 h / 0 - 20 °C 2: potassium carbonate / acetone / 12 h / Reflux 3: sodium dihydrogenphosphate; sodium chlorite / dimethyl sulfoxide; water / 14 h / 20 °C 4: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / 750.08 Torr View Scheme
Multi-step reaction with 2 steps 1: trichlorophosphate / 8.5 h / 0 - 20 °C / Inert atmosphere 2: sodium chlorite; sodium dihydrogen phosphate monohydrate / water; dimethyl sulfoxide / 20 °C / Inert atmosphere View Scheme

2,4-bis(benzyloxy)-6-pentylbenzaldehyde → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium dihydrogenphosphate; sodium chlorite / dimethyl sulfoxide; water / 14 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C / 750.08 Torr View Scheme

hexanoyl-CoA → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
With polyketide synthase; malonyl-CoA Enzymatic reaction;

2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester (38862-65-6) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 18 h / Reflux 2: potassium hydroxide; water / dimethyl sulfoxide / 18 h / 90 °C 3: hydrogen; palladium on activated charcoal / ethyl acetate / 18 h View Scheme

ethyl 2,4-dibenzyloxy-6-pentylbenzoate (104307-49-5) → 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide; water / dimethyl sulfoxide / 18 h / 90 °C 2: hydrogen; palladium on activated charcoal / ethyl acetate / 18 h View Scheme

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) + acetone (67-64-1) → 7-hydroxy-2,2-dimethyl-5-pentyl-4H-benzo[d][1,3]dioxin-4-one

Conditions	Yield
With dmap; thionyl chloride In 1,2-dimethoxyethane at 0 - 20℃; for 2h;	98%
With dmap; thionyl chloride In 1,2-dimethoxyethane at 0 - 20℃; for 2h;	39%

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) + benzyl bromide (100-39-0) → benzyl 2,4-bis(benzyloxy)-6-pentylbenzoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	98%

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) + benzyl bromide (100-39-0) → benzyl 2,4-dihydroxy-6-pentylbenzoate (53530-24-8)

Conditions	Yield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 5h;	92%

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) + cyclopentanone (120-92-3) → 7-hydroxy-5-pentyl-spiro[1,3-benzodioxine-2,1'-cyclopentane]-4-one

Conditions	Yield
With dmap; thionyl chloride In 1,2-dimethoxyethane at 0 - 20℃; for 2h;	46%

Methoxyacetone (5878-19-3) + 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → 7-hydroxy-2-(methoxymethyl)-2-methyl-5-pentyl-1,3-benzodioxin-4-one

Conditions	Yield
With dmap; thionyl chloride In 1,2-dimethoxyethane at 0 - 20℃; for 3h;	46%

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) + acetylacetone (123-54-6) → 2-acetonyl-7-hydroxy-2-methyl-5-pentyl-1,3-benzodioxin-4-one

Conditions	Yield
With dmap; thionyl chloride In 1,2-dimethoxyethane at 0 - 20℃; for 3h;	40%

diazomethane (186581-53-3, 908094-01-9) + 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → methyl 2,4-dihydroxy-6-pentylbenzoate (58016-28-7)

Conditions	Yield
With diethyl ether

diazomethane (186581-53-3, 908094-01-9) + 2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → 2,4-dimethoxy-6-pentylbenzoic acid methyl ester (63953-83-3)

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → benzyl 4-((2,4-bis(benzyloxy)-6-pentylbenzoyl)oxy)-2-hydroxy-6-pentylbenzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 5 h / 20 °C 2: trifluoroacetic anhydride / toluene / 20 °C View Scheme

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → anziaic acid (641-68-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 5 h / 20 °C 2: trifluoroacetic anhydride / toluene / 20 °C 3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C / 750.08 Torr View Scheme

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → benzyl 4-((2,4-bis(benzyloxy)benzoyl)oxy)-2-hydroxy-6-pentylbenzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 5 h / 20 °C 2: trifluoroacetic anhydride / toluene / 20 °C View Scheme

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → 2,2-dimethyl-4-oxo-5-pentyl-4H-benzo[d][1,3]dioxin-7-yl 2,4-bis(benzyloxy)-6-pentylbenzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap; thionyl chloride / 1,2-dimethoxyethane / 2 h / 0 - 20 °C 2: trifluoroacetic anhydride / toluene / 20 °C View Scheme

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → 4-((2,4-dihydroxybenzoyl)oxy)-2-hydroxy-6-pentylbenzoic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 5 h / 20 °C 2: trifluoroacetic anhydride / toluene / 20 °C 3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C / 750.08 Torr View Scheme

2,4-dihydroxy-6-pentylbenzoic acid (491-72-5) → 2,2-dimethyl-4-oxo-5-pentyl-4H-benzo[d][1,3]dioxin-7-yl 2,4-dihydroxy-6-pentylbenzoate

Conditions	Yield
Multi-step reaction with 3 steps 1: dmap; thionyl chloride / 1,2-dimethoxyethane / 2 h / 0 - 20 °C 2: trifluoroacetic anhydride / toluene / 20 °C 3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C / 750.08 Torr View Scheme

Upstream product

• 86791-41-5 2,4-dihydroxy-3,5-dibromo-6-pentylbenzoic acid 
• 104307-49-5 ethyl 2,4-dibenzyloxy-6-pentylbenzoate 
• 38862-65-6 2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 104307-50-8 2,4-bis(benzyloxy)-6-pentylbenzoic acid 
• 500-66-3 Olivetol 
• 855875-40-0 2,4-dihydroxyl-6-pentylbenzaldehyde 
• 58497-40-8 3,5-dibromo-2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 552-49-8 glomelliferic acid 
• 529-47-5 2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid 
• 75-65-0 tert-butyl alcohol 
• 491-47-4 olivetoric acid 
• 641-68-9 anziaic acid 
• 64-17-5 ethanol 
• 56542-16-6 semicarbazide acetate 

Downstream Products

• 641-68-9 anziaic acid 
• 53530-24-8 benzyl 2,4-dihydroxy-6-pentylbenzoate 
• 1244-58-2 cannabidiolic acid 
• 64750-25-0 benzyl 4,6-bis(benzyloxy)-3-hydroxy-2-pentylbenzoate 
• 1372167-27-5 lobarin 
• 64750-24-9 benzyl 4,6-bis(benzyloxy)-3-formyl-2-pentylbenzoate 
• 522-53-2 lobaric acid 
• 23978-85-0 Δ⁹-tetrahydrocannabinolic acid 
• 25555-57-1 CBGA 
• 63953-83-3 2,4-dimethoxy-6-pentylbenzoic acid methyl ester 
• 58016-28-7 methyl 2,6-dihydroxy-6-pentylbenzoate 

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