500-66-3

Basic information

• Product Name: Olivetol
• Synonyms: AURORA KA-7378;5-PENTYLRESORCINOL;5-PENTYL 1,3-BENZENEDIOL;5-N-PENTYLRESORCINOL;5-AMYL RESORCINOL;3,5-dihydroxyamylbenzene;OLIVETOL;5-n-amylresorcinol
• CAS NO: 500-66-3
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.24
• EINECS: 207-908-8
• Product Categories: API intermediates;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 500-66-3.mol
• Article Data: 26

Chemical Properties

• Melting Point: 46-48 °C(lit.)
• Boiling Point: 313.259 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: light purple to brown crystalline mass
• Density: 1.069 g/cm³
• Vapor Pressure: 0.000273mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.59±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: Olivetol(CAS DataBase Reference)
• NIST Chemistry Reference: Olivetol(500-66-3)
• EPA Substance Registry System: Olivetol(500-66-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/39
• WGK Germany: 3
• RTECS: VH2880000
• Hazardous Substances Data: 500-66-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Olivetol is used as a template molecule in the synthesis of molecularly imprinted polymer (MIP) for the development of drug delivery systems and sensors. MIPs are materials with specific binding sites that can selectively recognize and bind target molecules, improving the efficiency and specificity of drug delivery.
Used in Enzyme Inhibition:
Olivetol is used as an inhibitor of (S)-mephenytoin 4'-hydroxylase activity of recombinant CYP2C19, a cytochrome P450 enzyme involved in the metabolism of various drugs. By inhibiting this enzyme, Olivetol can modulate drug metabolism and potentially reduce drug-drug interactions, improving the safety and efficacy of certain medications.

Preparation

olivetol can also be formed through hydrolysis of intermediate polyketide CoAs or spontaneous cyclization.

Synthesis Reference(s)

The Journal of Organic Chemistry, 42, p. 3456, 1977 DOI: 10.1021/jo00441a036

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.

InChI:InChI=1/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3

Synthetic route

1,3-dimethoxy-5-pentylbenzene (22976-40-5) → Olivetol (500-66-3)

Conditions	Yield
With boron tribromide In dichloromethane at -15 - 20℃; for 1.5h; Solvent; Reagent/catalyst; Inert atmosphere;	95%
With boron tribromide In dichloromethane at -15 - 20℃; for 1.5h; Inert atmosphere;	92%
With boron tribromide In dichloromethane at -15 - 20℃; for 1.5h; Inert atmosphere;	92%

methyl 2,4-dihydroxy-6-pentylbenzoate (58016-28-7) → Olivetol (500-66-3)

Conditions	Yield
With water; potassium hydroxide at 50 - 100℃;	94%

1,3-Bis-benzyloxy-5-((Z)-pent-1-enyl)-benzene → Olivetol (500-66-3)

Conditions	Yield
With sodium; butan-1-ol at 80 - 90℃; for 1h;	81%
With hydrogen; palladium on activated charcoal In ethanol Yield given;

3,5-diamino-1-pentylbenzene → Olivetol (500-66-3)

Conditions	Yield
Stage #1: 3,5-diamino-1-pentylbenzene With sulfuric acid; sodium nitrite In dichloromethane at 5℃; Stage #2: With sulfuric acid; sodium sulfate In water for 1h; Reflux;	78%

methyl 6-n-pentyl-2-hydroxy-4-oxo-cyclohex-2-ene-1-carboxylate (27871-89-2) → Olivetol (500-66-3)

Conditions	Yield
With bromine In N,N-dimethyl-formamide at 160℃; for 10h; Cooling with ice;	69.3%
With bromine In N,N-dimethyl-formamide at 80 - 160℃;	69.3%
With bromine In N,N-dimethyl-formamide at 160℃; for 11.5h; Cooling with ice;	69.3%
With bromine In N,N-dimethyl-formamide at 160℃; for 10h; Cooling with ice;	69.3%
With bromine In N,N-dimethyl-formamide at 80 - 160℃; for 11.5h; Cooling with ice;	69.3%

4-Benzenesulfinyl-5-pentyl-cyclohexane-1,3-dione (74732-76-6) → Olivetol (500-66-3)

Conditions	Yield
With calcium carbonate In benzene for 5h; Heating;	48%

5-n-amyl-2-bromocyclohex-2-ene-3-ol-1-one (58016-30-1) → 4-bromo-5-pentylbenzene-1,3-diol (78463-35-1) + 4,6-dibromo-5-pentylbenzene-1,3-diol (78463-34-0) + Olivetol (500-66-3)

Conditions	Yield
In diphenylether heating to 155 deg C during 1 h;	A 32% B 10% C 40%

methanol (67-56-1) + olivetoric acid (491-47-4) → 6,8-dihydroxy-3-pentyl-1H-2-benzopyran-1-one (3734-54-1) + Olivetol (500-66-3)

Conditions	Yield
at 150 - 200℃;

formic acid (64-18-6) + olivetoric acid (491-47-4) → 6,8-dihydroxy-3-pentyl-1H-2-benzopyran-1-one (3734-54-1) + Olivetol (500-66-3)

CBD (13956-29-1) + pyridine hydrochloride (628-13-7) → 4-methylisopropylbenzene (99-87-6) + Olivetol (500-66-3)

Conditions	Yield
at 210 - 230℃;

2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester (38862-65-6) → Olivetol (500-66-3)

Conditions	Yield
With sodium hydroxide
With sodium hydroxide
With sodium hydroxide In water Heating;

5-n-amyl-2-bromocyclohex-2-ene-3-ol-1-one (58016-30-1) → Olivetol (500-66-3)

Conditions	Yield
With N,N-dimethyl-formamide

2-Hydroxy-4-oxo-6-pentyl-cyclohex-2-enecarboxylic acid ethyl ester (751419-63-3) → Olivetol (500-66-3)

Conditions	Yield
(i) CuBr2, DME, (ii) (heating in DMF), (iii) aq. NaOH; Multistep reaction;

n-butyllithium (109-72-8, 29786-93-4) + O-methylorcinol (3209-13-0) → Olivetol (500-66-3)

Conditions	Yield
Yield given. Multistep reaction;

Non-3-en-2-on (14309-57-0) + methyl 2-phenylsulfinylacetate (14090-83-6) → (4S,5S)-4-Benzenesulfinyl-3-hydroxy-5-pentyl-cyclohex-2-enone (67222-03-1, 74779-22-9, 74779-23-0) + (4S,5R)-4-Benzenesulfinyl-3-hydroxy-5-pentyl-cyclohex-2-enone (67222-03-1, 74779-22-9, 74779-23-0) + Olivetol (500-66-3)

Conditions	Yield
With magnesium methanolate In methanol 1.) 1 h, 2.) room temperature, 2 d; Yield given. Yields of byproduct given;

2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid (529-47-5) → 3-hydroxy-5-pentylphenyl 2,4-dihydroxy-6-pentylbenzoate + 2'-O-methylperlatolol + Olivetol (500-66-3)

Conditions	Yield
at 160℃; for 1h; Product distribution; pyrolysis; rate of decarboxylation;

methyl 2,6-dihydroxy-4-pentylbenzoate (83578-32-9) → Olivetol (500-66-3)

Conditions	Yield
With sodium hydroxide In methanol; water

diethyl 1,3-acetonedicarboxylate (105-50-0) + 3-oxo-octanoic acid (1)-ethyl ester → Olivetol (500-66-3)

Conditions	Yield
With sodium at 140 - 150℃; Erhitzen des Reaktionsprodukts mit KOH auf 250grad;

2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid (529-47-5) + aqueous KOH-solution → 2-hydroxy-4-methoxy-6-pentylbenzoic acid (52189-68-1) + Olivetol (500-66-3)

methanol (67-56-1) + olivetoric acid (491-47-4) → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + Olivetol (500-66-3) + olivetonide

Conditions	Yield
at 150℃; im Rohr;

formic acid (64-18-6) + olivetoric acid (491-47-4) → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + Olivetol (500-66-3) + olivetonide

3,5-dimethoxybenzyl alcohol (705-76-0) → Olivetol (500-66-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: Et3N / tetrahydrofuran / 1 h / 0 - 20 °C 2: 41 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 3: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 4: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 5: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme
Multi-step reaction with 3 steps 1: PBr3 2: CuI 3: aq. HCl, Py View Scheme

3,5-dimethoxybenzyl trimethylsilyl ether (185249-83-6) → Olivetol (500-66-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 41 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 2: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 3: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 4: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

1,3-dimethoxy-5-(2'-hydroxypentyl)benzene (185249-84-7) → Olivetol (500-66-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / Et3N / tetrahydrofuran / 1.08 h / 0 °C 2: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 3: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

Methanesulfonic acid 1-(3,5-dimethoxy-benzyl)-butyl ester (185249-86-9) → Olivetol (500-66-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / NaI, Zn / 1,2-dimethoxy-ethane / 8 h / Heating 2: 81 percent / 45percent HBr, glacial AcOH / 3 h / Heating View Scheme

3,5-dimethoxybenzaldehdye (7311-34-4) → Olivetol (500-66-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 2: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 3: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

1-(1-hydroxypentyl)-3,5-dimethoxybenzene (38228-28-3) → Olivetol (500-66-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 2: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

3,5-dimethoxybenzoic acid (1132-21-4) → Olivetol (500-66-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 89 percent / (COCl)2 / benzene / 2 h, room t., 1 h, reflux 2: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 3: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 4: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 5: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme
Multi-step reaction with 7 steps 4: 28.8 g / fluoroboric acid, sodium nitrite / H2O 5: 7.6 g / warming, distillation 6: 60 percent / lithium chips / 0.5 h 7: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme
Multi-step reaction with 4 steps 1: LiAlH4 2: PBr3 3: CuI 4: aq. HCl, Py View Scheme

3,5-dimethoxybenzoyl chloride (17213-57-9) → Olivetol (500-66-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 2: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 3: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 4: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme
Multi-step reaction with 6 steps 3: 28.8 g / fluoroboric acid, sodium nitrite / H2O 4: 7.6 g / warming, distillation 5: 60 percent / lithium chips / 0.5 h 6: boron tribromide, pyridine hydrochloride / CH2Cl2 / 24 h / -78 °C View Scheme

dimethyl sulfate (77-78-1) + Olivetol (500-66-3) → 1,3-dimethoxy-5-pentylbenzene (22976-40-5)

Conditions	Yield
With potassium carbonate In acetone at 60℃; for 4h;	98%
With potassium carbonate In acetone at 80℃; for 12.083h; Inert atmosphere;	98%
With potassium carbonate In acetone for 4h; Heating;	89%

chloromethyl methyl ether (107-30-2) + Olivetol (500-66-3) → 1,3-Bis(methoxymethoxy)-5-pentylbenzene (94450-80-3)

Conditions	Yield
Stage #1: Olivetol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide at 25℃; Inert atmosphere;	97%
Stage #1: Olivetol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;	92%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 16h; Ambient temperature;	91%

4-cyanobenzyl bromide (17201-43-3) + Olivetol (500-66-3) → 1,3-bis{4-cyanobenzyloxy}-5-(n-pentyl)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	95%

2,6-dichloropyridine-3,5-dicarbonitrile (151229-84-4) + Olivetol (500-66-3) → 25,27-diaza-4,6,16,18-tetracyano-11,23-di-n-pentyl-2,8,14,20-tetraoxacalix[4]arene

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 25℃; for 0.5h;	93%

Olivetol (500-66-3) → 1,3-dihydroxy-2-iodo-5-pentylbenzene (112639-12-0)

Conditions	Yield
With iodine; sodium hydrogencarbonate In tert-butyl methyl ether; water at 0℃; for 1h; Reagent/catalyst; Solvent; Temperature;	92%
With N-iodo-succinimide In methanol at 0℃; for 18h;	85%
With 18-crown-6 ether; 3-chloro-benzenecarboperoxoic acid; potassium iodide In dichloromethane 1) room temp., 2) 0 deg C, 15 min.;	82%
With 3-chloro-benzenecarboperoxoic acid; potassium iodide In dichloromethane at 0℃; for 0.333333h;	67%

1,5-difluoro-2,4-dinitrobenzene (327-92-4) + Olivetol (500-66-3) → C34H32N4O12

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 25℃; for 0.25h;	91%

ethyl vinyl ether (109-92-2) + Olivetol (500-66-3) → 1,3-bis(1-ethoxyethoxy)-5-pentylbenzene (125265-27-2)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane; N,N-dimethyl-formamide at 0℃; for 7h; Inert atmosphere;	91%

4,6-dichloropyrimidine (1193-21-1) + Olivetol (500-66-3) → 4,6,16,18-tetraaza-11,23-di-n-pentyl-2,8,14,20-tetraoxacalix[4]arene

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 18h;	90%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + Olivetol (500-66-3) → 2,4-dihydroxy-6-pentylbenzaldehyde (855875-40-0)

Conditions	Yield
With trichlorophosphate at 0 - 20℃; for 8.5h; Vilsmeier-Haack Formylation; Inert atmosphere; regioselective reaction;	90%
With trichlorophosphate at 0 - 20℃; for 18h; Vilsmeier-Haack Formylation;	56%

[1,3]-dioxolan-2-one (96-49-1) + Olivetol (500-66-3) → 2,2'-((5-pentyl-1,3-phenylene)bis(oxy))bis(ethan-1-ol)

Conditions	Yield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 170℃; for 1h; Inert atmosphere; Schlenk technique;	90%

2,6-dichloropyrazine (4774-14-5) + Olivetol (500-66-3) → 5,17,25,27-tetraaza-11,23-di-n-pentyl-2,8,14,20-tetraoxacalix[4]arene

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 18h;	89%

2,3,5,6-tetrachloropyridine (2402-79-1) + Olivetol (500-66-3) → 25,27-diaza-4,6,16,18-tetrachloro-11,23-di-n-pentyl-2,8,14,20-tetraoxacalix[4]arene

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 18h;	88%

Olivetol (500-66-3) → 4,6-dibromo-5-pentylbenzene-1,3-diol (78463-34-0)

Conditions	Yield
With hydrogen bromide In dimethyl sulfoxide; ethyl acetate at 60℃; for 1h; Temperature; Solvent;	87%
With bromine In dichloromethane at -15℃; Large scale;	82%
With bromine In dichloromethane at -30 - -28℃; for 0.75h;	73%

Olivetol (500-66-3) + methyl iodide (74-88-4) → 1,3-dimethoxy-5-pentylbenzene (22976-40-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	85%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 - 5h;

trans/cis-isopiperitenol (491-05-4, 4017-76-9, 4017-77-0, 65733-29-1, 65733-30-4, 74410-00-7, 96555-02-1, 115362-62-4, 141316-25-8) + Olivetol (500-66-3) → (+)-(3S,4S)-delta-1-tetrahydrocannabinol (17766-02-8)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; diastereoselective reaction;	85%

carbon dioxide (124-38-9) + Olivetol (500-66-3) → 2,6-dihydroxy-4-pentylbenzoic acid (61695-63-4)

Conditions	Yield
With potassium hydrogencarbonate In glycerol at 145℃; for 5h;	84%

trans/cis-isopiperitenol (491-05-4, 4017-76-9, 4017-77-0, 65733-29-1, 65733-30-4, 74410-00-7, 96555-02-1, 115362-62-4, 141316-25-8) + Olivetol (500-66-3) → (+)-Δ8-trans-tetrahydrocannabinol (33029-18-4)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; diastereoselective reaction;	84%

ethyl 2-oxocyclohexane carboxylate (1655-07-8) + Olivetol (500-66-3) → 1-hydroxy-3-pentyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one (40683-93-0)

Conditions	Yield
Stage #1: ethyl 2-oxocyclohexane carboxylate; Olivetol With trichlorophosphate In toluene at 20℃; for 38h; Stage #2: With water In toluene for 0.5h;	82%
With trichlorophosphate; benzene
With sulfuric acid

(+)-p-menthadiene-3-ol (491-05-4, 4017-76-9, 4017-77-0, 65733-29-1, 65733-30-4, 74410-00-7, 96555-02-1, 115362-62-4, 141316-25-8) + Olivetol (500-66-3) → dronabinol (1972-08-3)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; diastereoselective reaction;	82%

(+)-p-menthadiene-3-ol (491-05-4, 4017-76-9, 4017-77-0, 65733-29-1, 65733-30-4, 74410-00-7, 96555-02-1, 115362-62-4, 141316-25-8) + Olivetol (500-66-3) → delta-8-tetrahydrocannabinol (5957-75-5)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; diastereoselective reaction;	82%

Geraniol (106-24-1) + Olivetol (500-66-3) → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 20℃; for 12h; Darkness;	80%
With toluene-4-sulfonic acid In chloroform at 20℃; for 12h; Darkness;	39.9%
With toluene-4-sulfonic acid In chloroform at 20℃; for 12h; Darkness;	39.9%

4-Methylbenzyl bromide (104-81-4) + Olivetol (500-66-3) → C19H24O2

Conditions	Yield
With potassium carbonate In acetone at 20 - 50℃;	80%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + Olivetol (500-66-3) → 5-Pentyl-O,O'-bis(4,6-dichlor-1,3,5-triazin-2-yl)-resorcin (205182-16-7)

Conditions	Yield
With 2,3,5-trimethyl-pyridine In acetone at 0℃; for 2h;	79.8%

(3S,4S)-p-menth-1-ene-3,8-diol (119678-35-2) + Olivetol (500-66-3) → 2-[(1S,6S)-6-(1-Hydroxy-1-methyl-ethyl)-3-methyl-cyclohex-2-enyl]-5-pentyl-benzene-1,3-diol (190083-64-8)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 7h;	79%
With toluene-4-sulfonic acid In dichloromethane at 0℃; for 7h; Alkylation;	79%

pyridine-2-sulfonyl chloride (66715-65-9) + 4-Methylbenzyl bromide (104-81-4) + Olivetol (500-66-3) → 3-((4-Methylbenzyl)oxy)-5-pentylphenyl pyridine-2-sulfonate

Conditions	Yield
Stage #1: Olivetol With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: 4-Methylbenzyl bromide In acetone at 50℃; Stage #3: pyridine-2-sulfonyl chloride Further stages;	78%

Upstream product

• 13956-29-1 CBD 
• 628-13-7 pyridine hydrochloride 
• 529-47-5 2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylbenzoic acid 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 185249-83-6 3,5-dimethoxybenzyl trimethylsilyl ether 
• 185249-84-7 1,3-dimethoxy-5-(2'-hydroxypentyl)benzene 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 17213-58-0 3,5-dimethoxybenzamide 
• 75996-26-8 azido(3,5-dimethoxyphenyl)methanone 
• 52189-63-6 3,5-dimethoxyfluorobenzene 
• 72470-95-2 3,5-dimethoxybenzenediazonium tetrafluoroborate 
• 38862-65-6 2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 64-18-6 formic acid 
• 491-47-4 olivetoric acid 

Downstream Products

• 855875-40-0 2,4-dihydroxyl-6-pentylbenzaldehyde 
• 56661-19-9 (+/-)-1-hydroxy-9-methyl-3-pentyl-7,8,9,10-tetrahydro-benzo[c]chromen-6-one 
• 18456-88-7 5-Pentyl-1,3-cyclohexanedione 
• 78463-35-1 4-bromo-5-pentylbenzene-1,3-diol 
• 61695-63-4 2,6-dihydroxy-4-pentylbenzoic acid 
• 87449-78-3 5-(2,6-Dihydroxy-4-pentylphenyl)pyrrolidin-2-one 
• 205182-16-7 5-Pentyl-O,O'-bis(4,6-dichlor-1,3,5-triazin-2-yl)-resorcin 
• 142-62-1 hexanoic acid 
• 56157-26-7 2,2-dimethyl-7-pentyl-5-chromenol 
• 74219-29-7 (1'S,2'S)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol 
• 145104-69-4 (4R)-4-(4-pentyl-2,6-dihydroxyphenyl)-6,6-dimethyl-2-norpinanone 
• 35408-03-8 (+)-apoverbenone 
• 6087-61-2 (+)-trans-Δ⁸-tetrahydrocannabinol 
• 1072940-20-5 C₁₆H₂₄O₂ 

Relevant articles and documents

Preparation method of 3,5-dihydroxyamylbenzene

The invention provides a preparation method of 3,5-dihydroxyamylbenzene. The preparation method comprises the following steps: with a 3,5-dialkoxy benzoate compound as a raw material, subjecting the 3,5-dialkoxy benzoate compound to reacting with valeronitrile to generate a beta-ketone nitrile compound, hydrolyzing a cyano group to generate a carboxylic acid compound, performing a decarboxylation reaction to obtain 3,5-dialkoxyphenylpentanone, performing Huang Ming-long reaction or catalytic hydrogenation to convert 3,5-dialkoxyphenylpentanone into 3,5-dialkoxyamylbenzene, and finally, reducing an alkoxy group into a phenolic hydroxyl group so as to obtain 3,5-dihydroxyamylbenzene. The preparation method provided by the invention overcomes the defects of high cost, complex route, low yield, poor purity and the like of traditional processes.

Synthesis method of 3, 5-dihydroxypentene benzene

The invention provides a synthesis method of 3, 5-dihydroxypentene benzene. The synthesis method comprises the following steps: reacting 3, 5-dimethoxyphenol used as a raw material with a sulfonate halide reagent to generate sulfonate, carrying out cross-coupling reaction with a nucleophilic reagent to introduce amyl, and finally reducing methoxyl into phenolic hydroxyl, thereby obtaining the product 3, 5-dihydroxypentene benzene. The synthesis method solves the defects of high cost, complex route, low yield, poor purity and the like of the traditional process.

Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core

Based on the significant anti-inflammatory activity of natural quinone primin (5a), series of 1,4-benzoquinones, hydroquinones, and related resorcinols were designed, synthesized, characterized and tested for their ability to inhibit the activity of cyclooxygenase (COX-1 and COX-2) and 5-lipoxygenase (5-LOX) enzymes. Structural modifications resulted in the identification of two compounds 5b (2-methoxy-6-undecyl-1,4-benzoquinone) and 6b (2-methoxy-6-undecyl-1,4-hydroquinone) as potent dual COX/5-LOX inhibitors. The IC50 values evaluated in vitro using enzymatic assay were for compound 5b IC50 = 1.07, 0.57, and 0.34 μM and for compound 6b IC50 = 1.07, 0.55, and 0.28 μM for COX-1, COX-2, and 5-LOX enzyme, respectively. In addition, compound 6d was identified as the most potent 5-LOX inhibitor (IC50 = 0.14 μM; reference inhibitor zileuton IC50 = 0.66 μM) from the tested compounds while its inhibitory potential against COX enzymes (IC50 = 2.65 and 2.71 μM for COX-1 and COX-2, respectively) was comparable with the reference inhibitor ibuprofen (IC50 = 4.50 and 2.46 μM, respectively). The most important structural modification leading to increased inhibitory activity towards both COXs and 5-LOX was the elongation of alkyl chain in position 6 from 5 to 11 carbons. Moreover, the monoacetylation in ortho position of bromo-hydroquinone 13 led to the discovery of potent (IC50 = 0.17 μM) 5-LOX inhibitor 17 (2-bromo-6-methoxy-1,4-benzoquinone) while bromination stabilized the hydroquinone form. Docking analysis revealed the interaction of compounds with Tyr355 and Arg120 in the catalytic site of COX enzymes, while the hydrophobic parts of the molecules filled the hydrophobic substrate channel leading up to Tyr385. In the allosteric catalytic site of 5-LOX, compounds bound to Tyr142 and formed aromatic interactions with Arg138. Taken together, we identified optimal alkyl chain length for dual COX/5-LOX inhibition and investigated other structural modifications influencing COX and 5-LOX inhibitory activity.

SYNTHESIS AND PURIFICATION OF CANNABIGEROL AND ITS APPLICATION

The present invention relates to a method for producing cannabigerol and purifying it from a reaction mixture. The present invention also relates to the cosmetic use of cannabigerol for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, in particular for reducing pigmentation of the skin, preferably for the improvement of the appearance of the skin in case of hyperpigmentation, lentigo or vitiligo. Furthermore, the present invention relates to cannabigerol for use in a therapeutic method for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, preferably for use in a therapeutic method for the treatment and/or prevention of malign skin disorders, in particular skin cancer.

3. 5 - Dihydroxy fifth heavenly stem benzene synthetic method

The invention provides a 3, 5 - dihydroxy fifth heavenly stem benzene synthetic method, through under the acid catalysis of benzene with a Friedel - crafts acylation reaction to obtain the [...], the acid is a Lewis acid; the obtained [...] nitration to obtain 3, 5 - dinitrobenzene pentanone; then into methylene carbonyl reduction after reduction of nitro, to obtain 3, 5 - diamino [...]; diazotisations 3, 5 - diamino [...] variable hydroxy obtain 3, 5 - dihydroxy fifth heavenly stem benzene. The invention raw materials used are cheap and easily obtained bulk chemical raw materials, every one-step reaction conditions are relatively mild, which belongs to the chemical industry a large number of applied to the conventional reaction. In accordance with the technique to obtain the final product 3, 5 - dihydroxy fifth heavenly stem benzene (Olivetol) high purity, can reach 98.5% or more, the single hetero in 0.3% to the inner.

Concise access to primin, miconidin and related natural resorcinols

An efficient and short synthetic procedures affording the biologically active natural products primin, miconidin, olivetol, grevillol, and cardol (adipostatin A) in high yields are reported. The two strategies involve Sonogashira and Suzuki cross-couplings as the crucial steps for the installation of the alkyl side-chains. Syntheses start from cheap, commercially available 1-bromo-3,5-dimethoxybenezene to obtain 1,3-dimethoxy-5-(alk-1-yn-1-yl)benzene as the key intermediate. This intermediate can be easily and economically oxidized to provide primin in excellent overall yield while avoiding undesired side products by the virtue of its symmetry. The demethylation of the key intermediate affords natural resorcinols olivetol, grevillol, and cardol, respectively. The reduction of primin provides its hydroquinone derivative miconidin.

BIOENZYMATIC SYNTHESIS OF THC-v, CBV AND CBN AND THEIR USE AS THERAPEUTIC AGENTS

The present invention provides methods for producing cannabinoids. More specifically, the invention is directed to the bio-enzymatic synthesis of THC-v, CBV and CBN by contacting a compound according to Formula I with a cannabinoid synthase enzyme. Also described is a system for producing these pharmaceutically important cannabinoids and the use of such cannabinoids as therapeutic agents.

BIOSYNTHESIS OF CANNABINOID PRODRUGS AND THEIR USE AS THERAPEUTIC AGENTS

The present invention provides methods for producing cannabinoid prodrugs. Also described are pharmaceuticals acceptable compositions of the prodrugs and a system for the large-scale production of the prodrugs.

METHODS FOR THE MANUFACTURE OF CANNABINOID PRODRUGS, PHARMACEUTICAL FORMULATIONS AND THEIR USE

Described are methods for producing cannabinoid prodrugs as well as methods for formulating such prodrugs in a pharmaceutically acceptable form and their use as therapeutic agents for treating diseases.

APPARATUS AND METHODS FOR THE SIMULTANEOUS PRODUCTION OF CANNABINOID COMPOUNDS

The present invention provides an apparatus and methods for simultaneously producing different compounds in various ratios under set conditions.