Cannabigerolic acid
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| Names
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Preferred IUPAC name
3-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-2,4-dihydroxy-6-pentylbenzoic acid
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| Identifiers
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CAS Number
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| Properties
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Chemical formula
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C22H32O4
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| Molar mass
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360.494 g·mol−1
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Cannabigerolic acid (CBGA) is the acidic form of cannabigerol (CBG). It is a dihydroxybenzoic acid and olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. It is a biosynthetic precursor to Delta-9-tetrahydrocannabinol, which is the principal psychoactive constituent of the Cannabis plant. It is also a meroterpenoid (i.e. a polyketide and a terpenoid), a member of resorcinols and a phytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.[1]
In the Cannabis plant, olivetolic acid and geranyl diphosphate are synthesized into CBGA.[2]: 6 [3]: 17 CBGA is converted in the plant by CBCA synthase, CBDA synthase and THCA synthase into CBCA, CBDA and THCA respectively.[2]: 6–7
References
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Phytocannabinoids (comparison) | | Cannabibutols | |
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| Cannabichromenes | |
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| Cannabicyclols | |
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| Cannabidiols | |
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| Cannabielsoins | |
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| Cannabigerols | |
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| Cannabiphorols | |
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| Cannabinols |
- CBN
- CBNA
- CBN-C1
- CBN-C2
- CBN-C4
- CBNM
- CBND
- CBNP
- CBVD
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| Cannabitriols | |
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| Cannabivarins | |
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| Delta-3-tetrahydrocannabinols | |
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| Delta-4-tetrahydrocannabinols | |
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| Delta-7-tetrahydrocannabinols | |
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| Delta-8-tetrahydrocannabinols | |
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| Delta-9-tetrahydrocannabinols | |
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| Delta-10-Tetrahydrocannabinols | |
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| Delta-11-Tetrahydrocannabinols | |
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| Miscellaneous cannabinoids | |
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| Active metabolites | |
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| Endocannabinoids | |
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Synthetic cannabinoid receptor agonists / neocannabinoids | Classical cannabinoids (dibenzopyrans) | |
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Non-classical cannabinoids | |
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| Adamantoylindoles | |
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| Benzimidazoles | |
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| Benzoylindoles |
- 1-Butyl-3-(2-methoxybenzoyl)indole
- 1-Butyl-3-(4-methoxybenzoyl)indole
- 1-Pentyl-3-(2-methoxybenzoyl)indole
- AM-630
- AM-679
- AM-694
- AM-1241
- AM-2233
- GW-405,833 (L-768,242)
- Pravadoline
- RCS-4
- WIN 54,461
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| Cyclohexylphenols | |
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| Eicosanoids |
- AM-883
- AM-1346
- ACEA
- ACPA
- Methanandamide (AM-356)
- O-585
- O-689
- O-1812
- O-1860
- O-1861
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Indazole-3- carboxamides | |
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| Indole-3-carboxamides | |
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| Indole-3-carboxylates | |
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| Naphthoylindazoles | |
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| Naphthoylindoles | |
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| Naphthoylpyrroles |
- JWH-030
- JWH-031
- JWH-032
- JWH-033
- JWH-036
- JWH-044
- JWH-045
- JWH-145
- JWH-146
- JWH-147
- JWH-150
- JWH-156
- JWH-243
- JWH-244
- JWH-245
- JWH-246
- JWH-292
- JWH-293
- JWH-307
- JWH-308
- JWH-309
- JWH-346
- JWH-347
- JWH-348
- JWH-363
- JWH-364
- JWH-365
- JWH-366
- JWH-367
- JWH-368
- JWH-369
- JWH-370
- JWH-371
- JWH-372
- JWH-373
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| Naphthylmethylindenes | |
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| Naphthylmethylindoles |
- JWH-175
- JWH-184
- JWH-185
- JWH-192
- JWH-194
- JWH-195
- JWH-196
- JWH-197
- JWH-199
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| Phenylacetylindoles | |
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| Pyrazolecarboxamides | |
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Tetramethylcyclo- propanoylindazoles | |
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Tetramethylcyclo- propanoylindoles | |
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| Others | |
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| Allosteric CBRTooltip Cannabinoid receptor ligands | |
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Endocannabinoid enhancers (inactivation inhibitors) | |
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Anticannabinoids (antagonists/inverse agonists/antibodies) | |
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| TRPA | | Activators |
- 4-Hydroxynonenal
- 4-Oxo-2-nonenal
- 5,6-EET
- 12S-HpETE
- 15-Deoxy-Δ12,14-prostaglandin J2
- α-Sanshool (ginger, Sichuan and melegueta peppers)
- Acrolein
- Allicin (garlic)
- Allyl isothiocyanate (mustard, radish, horseradish, wasabi)
- AM404
- ASP-7663
- Bradykinin
- Cannabichromene (cannabis)
- Cannabidiol (cannabis)
- Cannabigerol (cannabis)
- Cinnamaldehyde (cinnamon)
- CR gas (dibenzoxazepine; DBO)
- CS gas (2-chlorobenzal malononitrile)
- Cuminaldehyde (cumin)
- Curcumin (turmeric)
- Dehydroligustilide (celery)
- Diallyl disulfide
- Dicentrine (Lindera spp.)
- Farnesyl thiosalicylic acid
- Formalin
- Gingerols (ginger)
- Hepoxilin A3
- Hepoxilin B3
- Hydrogen peroxide
- Icilin
- Isothiocyanate
- JT-010
- Ligustilide (celery, Angelica acutiloba)
- Linalool (Sichuan pepper, thyme)
- Methylglyoxal
- Methyl salicylate (wintergreen)
- N-Methylmaleimide
- Nicotine (tobacco)
- Oleocanthal (olive oil)
- Paclitaxel (Pacific yew)
- Paracetamol (acetaminophen)
- PF-4840154
- Phenacyl chloride
- Polygodial (Dorrigo pepper)
- Shogaols (ginger, Sichuan and melegueta peppers)
- Tear gases
- Tetrahydrocannabinol (cannabis)
- Tetrahydrocannabiorcol
- Thiopropanal S-oxide (onion)
- Umbellulone (Umbellularia californica)
- WIN 55,212-2
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| Blockers | |
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| TRPC | |
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| TRPM | | Activators |
- ADP-ribose
- BCTC
- Calcium (intracellular)
- CIM-0216
- Cold
- Coolact P
- Cooling Agent 10
- Eucalyptol (eucalyptus)
- Frescolat MGA
- Frescolat ML
- Geraniol
- Hydroxycitronellal
- Icilin
- Linalool
- Menthol (mint)
- PMD 38
- Pregnenolone sulfate
- Rutamarin (Ruta graveolens)
- Steviol glycosides (e.g., stevioside) (Stevia rebaudiana)
- Sweet tastants (e.g., glucose, fructose, sucrose; indirectly)
- Thio-BCTC
- WS-12
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| Blockers | |
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| TRPML | |
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| TRPP | |
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| TRPV | | Activators |
- 2-APB
- 5,6-EET
- 9-HODE
- 9-oxoODE
- 12S-HETE
- 12S-HpETE
- 13-HODE
- 13-oxoODE
- 20-HETE
- α-Sanshool (ginger, Sichuan and melegueta peppers)
- Allicin (garlic)
- AM404
- Anandamide
- Bisandrographolide (Andrographis paniculata)
- Camphor (camphor laurel, rosemary, camphorweed, African blue basil, camphor basil)
- Cannabidiol (cannabis)
- Cannabidivarin (cannabis)
- Capsaicin (chili pepper)
- Carvacrol (oregano, thyme, pepperwort, wild bergamot, others)
- DHEA
- Diacyl glycerol
- Dihydrocapsaicin (chili pepper)
- Estradiol
- Eugenol (basil, clove)
- Evodiamine (Euodia ruticarpa)
- Gingerols (ginger)
- GSK1016790A
- Heat
- Hepoxilin A3
- Hepoxilin B3
- Homocapsaicin (chili pepper)
- Homodihydrocapsaicin (chili pepper)
- Incensole (incense)
- Lysophosphatidic acid
- Low pH (acidic conditions)
- Menthol (mint)
- N-Arachidonoyl dopamine
- N-Oleoyldopamine
- N-Oleoylethanolamide
- Nonivamide (PAVA) (PAVA spray)
- Nordihydrocapsaicin (chili pepper)
- Paclitaxel (Pacific yew)
- Paracetamol (acetaminophen)
- Phenylacetylrinvanil
- Phorbol esters (e.g., 4α-PDD)
- Piperine (black pepper, long pepper)
- Polygodial (Dorrigo pepper)
- Probenecid
- Protons
- RhTx
- Rutamarin (Ruta graveolens)
- Resiniferatoxin (RTX) (Euphorbia resinifera/pooissonii)
- Shogaols (ginger, Sichuan and melegueta peppers)
- Tetrahydrocannabivarin (cannabis)
- Thymol (thyme, oregano)
- Tinyatoxin (Euphorbia resinifera/pooissonii)
- Tramadol
- Vanillin (vanilla)
- Zucapsaicin
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See also: Receptor/signaling modulators • Ion channel modulators |