25654-31-3

Usage

Uses

Cannabigerol is a partial agonist of CB2 and CB1 receptors (Ki values are 337 and 440 nM respectively). Cannabigerol also exhibits α2-adrenoceptor agonist activity (EC50 = 0.2 nM in mouse brain membra nes).

Definition

ChEBI: A natural product found in Cannabis sativa and Helichrysum species.

General Description

A non-psychoactive cannabinoid found in Cannabis, Cannabigerol (CBG) reportedly has efficacy for medical conditions such as glaucoma and inflammatory bowel disease. This Certified Spiking Solution? is suitable for cannabigerol testing methods by HPLC, GC/MS or LC-MS/MS for forensic analysis, clinical toxicology, urine drug testing, and Cannabis potency or impurity profiling testing applications. Cerilliant solution Certified Reference Materials (CRMs) of cannabinoids are supplied in a convenient, quantitative, US DEA-exempt solution format and with TK#s for Canadian customers.

InChI:InChI=1/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+

Synthetic route

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%

(E)-8-(3,7-dimethylocta-2,6-dien-1-yl)-7-hydroxy-2,2-dimethyl-5-pentyl-4H-benzo[d][1,3]dioxin-4-one → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With water; potassium hydroxide In 1,4-dioxane at 120℃; for 18h; Sealed tube;	64%

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) + C31H48O2

Conditions	Yield
With aluminum oxide In 1,2-dichloro-ethane for 6h; Solvent; Reflux;	A 62% B 10 %Spectr.

4,6-dibromocannabigerol → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With sodium L-ascorbate; triethylamine; sodium sulfite In methanol; water at 75℃; for 24h;	5.95%

(E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid methyl ester (63953-93-5) → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With sodium hydroxide In methanol

geranyl diphosphate (763-10-0) + Olivetol (500-66-3) → C21H32O2 (55854-24-5) + 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With Tris-HCl buffer; magnesium chloride at 25℃; pH=9.0; Enzyme kinetics;
With Tris-HCl buffer; magnesium chloride at 25℃; pH=9.0;

C22H32O3 → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate 2: potassium hydroxide; water / methanol 3: potassium hydroxide; water / methanol / Heating View Scheme
Multi-step reaction with 4 steps 1: alkaline condition 2: aminosulfonic acid; water / tetrahydrofuran; dimethyl sulfoxide 3: potassium hydroxide; water / methanol 4: potassium hydroxide; water / methanol / Heating View Scheme

C26H36O5 → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: aminosulfonic acid; water / tetrahydrofuran; dimethyl sulfoxide 2: potassium hydroxide; water / methanol 3: potassium hydroxide; water / methanol / Heating View Scheme

C26H36O6 → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide; water / methanol 2: potassium hydroxide; water / methanol / Heating View Scheme

CBGA (25555-57-1) → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With water; potassium hydroxide In methanol Heating;

C22H32O3 → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: florisil 2: potassium carbonate 3: potassium hydroxide; water / methanol 4: potassium hydroxide; water / methanol / Heating View Scheme
Multi-step reaction with 5 steps 1: florisil 2: alkaline condition 3: aminosulfonic acid; water / tetrahydrofuran; dimethyl sulfoxide 4: potassium hydroxide; water / methanol 5: potassium hydroxide; water / methanol / Heating View Scheme

Geraniol (106-24-1) + Olivetol (500-66-3) → C21H32O2 (55854-24-5) + 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 55℃; for 5h; Temperature; Solvent; Reagent/catalyst;

Geraniol (106-24-1) + Olivetol (500-66-3) → C21H32O2 (55854-24-5) + 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) + C31H48O2

Conditions	Yield
With toluene-4-sulfonic acid In chloroform at 20℃; for 12h; Solvent; Darkness;	A 280 mg B 420 mg C 712 mg

trans-geranyl bromide (6138-90-5) → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) / water; butan-1-ol / 18 h / 60 °C / Sealed tube 2: methanesulfonic acid / methanol; diethyl ether / 4 °C / Sealed tube View Scheme

trans-geranyl bromide (6138-90-5) + Olivetol (500-66-3) → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With potassium carbonate In tert-butyl methyl ether at 20℃; Reagent/catalyst; Solvent;

1,3-bis(methoxymethyl ether)cannabigerol → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With methanesulfonic acid In methanol; diethyl ether at 4℃; Sealed tube;

1,3-bis[2-(trimethylsiloxy)methoxyethyl]cannabigerol → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
With methanesulfonic acid In methanol; diethyl ether at 4℃; Sealed tube;

C29H55BO6Si2 → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) / water; butan-1-ol / 18 h / 60 °C / Sealed tube 2: methanesulfonic acid / methanol; diethyl ether / 4 °C / Sealed tube View Scheme

1,3-Bis(methoxymethoxy)-5-pentylbenzene (94450-80-3) → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Sealed tube 1.2: 0 - 20 °C / Sealed tube 1.3: 0.5 h 2.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 17 h / 80 °C / Sealed tube 3.1: methanesulfonic acid / methanol; diethyl ether / 4 °C / Sealed tube View Scheme

3,7-dimethylocta-1,6-dien-3-ol (78-70-6) + Olivetol (500-66-3) → 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) + abnormal-CBG

Conditions	Yield
With MP-TsOH resin In ethyl acetate Flow reactor; Overall yield = 40 percent;	A 35 mg B 35 mg

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) + magnesium methyl carbonate (4861-79-4) → CBGA (25555-57-1)

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 1h;	90%
In N,N-dimethyl-formamide at 120℃; for 1h;
In N,N-dimethyl-formamide at 120℃; for 1h;
In N,N-dimethyl-formamide at 130℃; for 3h;

carbon dioxide (124-38-9) + 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) + magnesium methanolate (109-88-6, 16436-83-2, 16436-85-4) → CBGA (25555-57-1)

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 3h; Sealed tube;	90%
Stage #1: carbon dioxide; 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol; magnesium methanolate at 50℃; for 3h; Sealed tube; Stage #2: With hydrogenchloride; water In methanol; chloroform pH=2;	37.5%

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 2-(3,7-dimethylocta-1,6-dienyl)-5-pentylresorcinol (95543-71-8)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In hexane at 50℃; for 1h;	80%

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → cannabigeroquinone

Conditions	Yield
With n-butyllithium; oxygen In N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 50℃; for 2h; Cooling with ice;	62%
With potassium tert-butylate; oxygen In toluene at 20℃; for 2h;	53%
With stabilized 1-hydroxy-1λ5,2-benziodoxole-1,3-dione, SIBX In ethyl acetate at 20℃; for 18h; Cooling with ice;	37%

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) + tert-butyldimethylsilyl chloride (18162-48-6) → C27H46O2Si

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃;	52%

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) + methyl iodide (74-88-4) → cannabigerol monomethyl ether (29106-17-0) + 1,3-bis(methoxy)cannabigerol (29106-16-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 3h;	A 35% B 40%

carbon dioxide (124-38-9) + 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → CBGA (25555-57-1)

Conditions	Yield
With magnesium methanolate at 50℃; for 3h; Reagent/catalyst; Temperature; Sealed tube;	37.5%
With magnesium methanolate at 50℃; for 3h; Sealed tube;

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → CBGA (25555-57-1)

Conditions	Yield
With carbon dioxide; magnesium methanolate In methanol; chloroform at 50℃; for 3h; Reagent/catalyst; Solvent; Temperature; Sealed tube;	37.5%

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 3,3'-bis((E)-3,7-dimethyl-octa-2,6-dienyl)-4,4'-dihydroxy-6,6'-dipentyl-1,1'-bi(cyclohexa-3,6-diene)-2,2',5,5'-tetraone

Conditions	Yield
With sodium hydride In toluene for 12h;	24%

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → cyclocannabigerol A + cyclocannabigerol B + iodocyclocannabigerol A + spirocannabigerol A + spirocannabigerol B + C28H40O2

Conditions	Yield
With iodine In toluene for 5h; Reflux;	A 2.3% B 8.1% C 14.8% D 0.7% E 1.3% F 3.2%

diazomethane (186581-53-3, 908094-01-9) + 2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → cannabigerol monomethyl ether (29106-17-0)

Conditions	Yield
In methanol

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → cannabichromene (20675-51-8, 4993-99-1)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 1h; Ambient temperature;

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 6-(3,7-dimethyl-octa-2,6-dienyl)-5-hydroxy-3-pentyl-2-ethylamino-[1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; oxygen / toluene / 2 h / 20 °C 2: oxygen / water; ethanol / 2 h / 20 °C View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 6-(3,7-dimethyl-octa-2,6-dienyl)-5-hydroxy-3-pentyl-2-pentylamino-[1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; oxygen / toluene / 2 h / 20 °C 2: oxygen / ethanol / 22 h / 20 °C View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 6-(3,7-dimethyl-octa-2,6-dienyl)-5-hydroxy-3-pentyl-2-isobutylamino[1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; oxygen / toluene / 2 h / 20 °C 2: oxygen / ethanol / 8 h / 20 °C View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 6-(3,7-dimethyl-octa-2,6-dienyl)-5-hydroxy-3-pentyl-2-butylamino [1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; oxygen / toluene / 2 h / 20 °C 2: oxygen / ethanol / 18 h / 20 °C View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 2-(3,7-dimethyl-octa-2,6-dienyl)-3-hydroxy-6-methylamino-5-pentyl-[1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; oxygen / toluene / 2 h / 20 °C 2: oxygen / ethanol / 6 h / 20 °C View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 2-(3,7-dimethyl-octa-2,6-dienyl)-3-hydroxy-6-isopropylamino-5-pentyl-[1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; oxygen / toluene / 2 h / 20 °C 2: oxygen / ethanol / 18 h / 20 °C View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 2-benzylamino-6-(3,7-dimethyl-octa-2,6-dienyl)-5-hydroxy-3-pentyl-[1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; oxygen / toluene / 2 h / 20 °C 2: oxygen / ethanol / 18 h / 20 °C View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → 2-(3,7-dimethyl-octa-2,6-dienyl)-6-(2,2-dimethyl-propylamino)-3-hydroxy-5-pentyl-[1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; oxygen / toluene / 2 h / 20 °C 2: oxygen / ethanol / 18 h / 20 °C View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → cannabidiolic acid (1244-58-2) + cannabichromenic acid

Conditions

Yield

Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1 h / 120 °C 2: 2-hydroxypropyl–β–cyclodextrin; MKCSTFSFWFVCKIIFFFFSFNIQTSIANPENFLKCFSQYIPNNATNLKLVYTQNPLYMSVLNSTIHNLRFTSDTTPKPLVIVTPSHVSHIQGTILCSKKVGLQIRTSGGHDSEGMSYISQFVIVDLRNMRSIKIDVHSQTAWVEAGATLGEVYYWVNEKNENLSLAAGYCPTVCAGGHFGGGGYGPLMRNYGLAADNIIDAHLWWGKVLDRKSMGEDLFWALRGGGAESFGIIVAWKIPLVAKSTMFSVKKIMEIHELVKLVNKWQNIAYKYDKDLLLMTHFITRNITDNQGKNKTAIHTYFSSWLGGVDSLVDLMNKSFPELGIKKTDCRQLSWIDTIIFYSGVVNYDTDNFNKEILLDRSAGQNGAFKIKLDYVKKPIPESWVQILEKLYEEDIGAGMYALYPYGGIMDEISESAIPFPHRAGILYELWYICSWEKQEDNEKHLNWIRNNFMTPYVSKNPRLAYLNYRDLDIGINDPKNPNNYTQARIWGEKGKNFDRLVKVKTLVDPNNFFRNEQSIPPLPRHRH / aq. phosphate buffer / 8 h / 30 °C / pH 4.2 / Large scale; Enzymatic reaction View Scheme

2-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-pentyl-benzene-1,3-diol (25654-31-3) → cannabichromenic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 3 h / 50 °C / Sealed tube 1.2: pH 2 2.1: 2-hydroxypropyl–β–cyclodextrin; MNCSAFSFWFVCKIIFFFLSFHIQISIANPRENFLKCFSKHIPNVANPKLVYTQHDQLYMSILNSTIQNLRFISDTTPKPLVIVTPSNSHIQATCSKKVGLQTRSGGFAEGMSYISQVPFVVVDLRNMHSIKIDVHSQTAWVEAGATLGEVYYWINEKNENLSFPGGYCPTVGVGGHFSGGGYGALMRNYGLAADNIIDAFILVNVDGKVLDPKSMGEDLFWAIRGGGGENFGIIAAWKIKLVASKSTIFSVKKNMEIHGLVKLFNKWQNIAYKYDKDLVLMTHFITKNITDNHGKNKTTVHGYFSSIFHGGVDSLDLMNKSFRELGIKKTDCKELSWIDTTIFYSGVVNYNTANFKKEDLDRSAGKKTAFSIKLDYVKKPIPETAMVKILEKLYEEDVGAGMYVLYPYGGIMEEISESAIPFPHRAGFYELWYTASWEKQEDNEKHINWVRSVYNFTTPYVSQNPRLAYLNYRDLDLGKTNHASPNNYTQARWGKWGKNFNRLVKVKTKVDPN FFRNEQSIPPLPPHHH / aq. phosphate buffer / 8 h / 30 °C / pH 5 / Large scale; Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 1 h / 120 °C 2: 2-hydroxypropyl–β–cyclodextrin; MNCSAFSFWFVCKIIFFFLSFHIQISIANPRENFLKCFSKHIPNVANPKLVYTQHDQLYMSILNSTIQNLRFISDTTPKPLVIVTPSNSHIQATCSKKVGLQTRSGGFAEGMSYISQVPFVVVDLRNMHSIKIDVHSQTAWVEAGATLGEVYYWINEKNENLSFPGGYCPTVGVGGHFSGGGYGALMRNYGLAADNIIDAFILVNVDGKVLDPKSMGEDLFWAIRGGGGENFGIIAAWKIKLVASKSTIFSVKKNMEIHGLVKLFNKWQNIAYKYDKDLVLMTHFITKNITDNHGKNKTTVHGYFSSIFHGGVDSLDLMNKSFRELGIKKTDCKELSWIDTTIFYSGVVNYNTANFKKEDLDRSAGKKTAFSIKLDYVKKPIPETAMVKILEKLYEEDVGAGMYVLYPYGGIMEEISESAIPFPHRAGFYELWYTASWEKQEDNEKHINWVRSVYNFTTPYVSQNPRLAYLNYRDLDLGKTNHASPNNYTQARWGKWGKNFNRLVKVKTKVDPN FFRNEQSIPPLPPHHH / aq. phosphate buffer / 8 h / 30 °C / pH 5 / Large scale; Enzymatic reaction View Scheme

Upstream product

• 106-24-1 Geraniol 
• 500-66-3 Olivetol 
• 763-10-0 geranyl diphosphate 
• 108-73-6 3,5-dihydroxyphenol 
• 308796-10-3 (1-pentyl)zinc(II) bromide 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 94450-80-3 1,3-Bis(methoxymethoxy)-5-pentylbenzene 
• 6138-90-5 trans-geranyl bromide 
• 25555-57-1 CBGA 
• 63953-93-5 (E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid methyl ester 

Downstream Products

• 95543-71-8 2-(3,7-dimethylocta-1,6-dienyl)-5-pentylresorcinol 
• 29106-17-0 cannabigerol monomethyl ether 
• 29106-16-9 1,3-bis(methoxy)cannabigerol 
• 20675-51-8 cannabichromene 
• 25555-57-1 CBGA 
• 1244-58-2 cannabidiolic acid 
• 1040411-87-7 C₂₅H₃₆O₄ 

Relevant academic research and scientific papers

Efficient synthesis of cannabigerol, grifolin, and piperogalin via alumina-promoted allylation

The synthesis of three phenolic natural products has been accomplished with unprecedented efficiency using a new alumina-promoted regioselective aromatic allylation reaction. Cannabigerol and grifolin were prepared in one step from the inexpensive 5-alkyl-resorcinols olivetol and orcinol. Piperogalin was synthesized, for the first time, via two sequential allylations of orcinol with geraniol and prenol.

Uncovering the Hidden Antibiotic Potential of Cannabis

The spread of antimicrobial resistance continues to be a priority health concern worldwide, necessitating the exploration of alternative therapies. Cannabis sativa has long been known to contain antibacterial cannabinoids, but their potential to address antibiotic resistance has only been superficially investigated. Here, we show that cannabinoids exhibit antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), inhibit its ability to form biofilms, and eradicate preformed biofilms and stationary phase cells persistent to antibiotics. We show that the mechanism of action of cannabigerol is through targeting the cytoplasmic membrane of Gram-positive bacteria and demonstrate in vivo efficacy of cannabigerol in a murine systemic infection model caused by MRSA. We also show that cannabinoids are effective against Gram-negative organisms whose outer membrane is permeabilized, where cannabigerol acts on the inner membrane. Finally, we demonstrate that cannabinoids work in combination with polymyxin B against multidrug resistant Gram-negative pathogens, revealing the broad-spectrum therapeutic potential for cannabinoids.

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

METHODS OF SYNTHESIZING CANNABIGERGOL, CANNABIGEROLIC ACID, AND ANALOGS THEREOF

Disclosed are methods for preparing carmabigerol (CBG) or a CBG analog, embodiments of the method comprising providing a compound (I); combining the compound (I) with geraniol and a solvent to form a reaction mixture; and combining the reaction mixture with an acid catalyst to form a product mixture comprising CBG or the CBG analog. The method may further comprise separating the CBG or the CBG analog for the product mixture and may further comprise purifying the CBG or CBG analog. Methods for preparing cannabigerolic acid (CBGA) or a CBGA analog are also disclosed. The present disclosure also provides high purity CBG, CBGA and analogs thereof. CBG can be useful as a neuroprotectant, an antibacterial agent, etc.

PREPARING AND MODIFYING MEROTERPENE POLYKETIDES, KETONES, AND LACTONES FOR CANNABINOID SEMISYNTHESIS

Provided herein are processes, including semi-synthetic, and synthetic processes for preparing cannabinoids, and cannabinoid compositions provided thereby.

CATALYTIC CANNABIGEROL PROCESSES AND PRECURSORS

The present disclosure relates to cannabigerol sulfonate esters and processes for their use to prepare cannabigerol (CBG) and related compounds, including cannabigerobutol (CBGB), cannabigerovarin (CBGV), and cannabigerophorbol (CBGP). In a preferred embodiment, the cannabigerol sulfonate ester is (E)-4-(3, 7-5 dimethylocta-2,6-dienyl)-3,5-bis(trimetbylsilyloxy)phenyl trifluoromethanesulfonate. In a preferred process, the trifluoromethansulfonate leaving group is replaced by an alkyl group. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabigerol and related compounds from the cannabigerol sulfonate esters.

PROCESS FOR THE PRODUCTION OF CANNABINOIDS AND CANNABINOID ACIDS

The present invention relates to a process for the preparation of diverse known and novel cannabinoids 5, which include cannabigerol (CBG, 1), cannabigerolic acid (CBGA, 2), cannabigerovarin (CBGV, 3), cannabigerovarinic acid (CBGVA, 4) and other naturally occurring monocyclic cannabinoids and other analogues from simple inexpensive starting materials using a cascade sequence of allylic rearrangement and aromatization. Novel cannabinoids of series 5 are also claimed as part of the invention. These synthesized cannabinoids, unlike the minor cannabinoids isolated from Cannabis saliva or synthesized from the condensation reactions such as the reactions of substituted resorcinols with monoterpenes, are much easier to obtain at high purity levels. In particular, these cannabinoids, including but not limited to cannabigerol (CBG, 1), cannabigerolic acid (CBGA, 2), cannabigerovarin (CBGV, 3) and cannabigerovarinic acid (CBGVA, 4) are obtained without contamination with impurities with variation in RA and RB (e.g. contamination of CBG with CBGV).

SYNTHESIS OF CANNABIGEROL

Multiple methods of synthesizing cannabigerol are presented. Combining olivetol with geraniol derivatives are provided. Cross-coupling methods of combing functionalized resorcinols are provided. Useful intermediates are formed during such cross-coupling steps.

CRYSTALLINE CANNABIGEROL

The application relates to crystalline cannabigerol comprising at least one X-ray powder diffraction peak selected from the group consisting of 4.73°, 9.52°, 14.30°, and 23.93° 2Θ (each ± 0.20° 2Θ), to methods of making the crystalline cannabigerol and its medical uses.

ONE-STEP FLOW-MEDIATED SYNTHESIS OF CANNABIDIOL (CBD) AND DERIVATIVES

Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.