Cannabichromenic acid

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Cannabichromenic acid
Cannabichromenic acid.svg
Names
IUPAC name
5-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromene-6-carboxylic acid
Other names
  • CBCA
  • (+)-Cannabichromenic acid
Identifiers
  • (±):185505-15-1
  • (+):20408-52-0 [1]
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C22H30O4/c1-5-6-7-10-16-14-18-17(20(23)19(16)21(24)25)11-13-22(4,26-18)12-8-9-15(2)3/h9,11,13-14,23H,5-8,10,12H2,1-4H3,(H,24,25)
    Key: HRHJHXJQMNWQTF-UHFFFAOYSA-N
  • (±):CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1C(=O)O)O
Properties
C22H30O4
Molar mass 358.478 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cannabichromenic acid (CBCA) is minor cannabinoid and precursor of cannabichromene. [2]

Contents

Biosynthesis

Geranyl pyrophosphate and olivetolic acid combine to produce cannabigerolic acid (CBGA; the sole intermediate for all other phytocannabinoids). The enzyme CBCA synthase can cyclize either cannabigerolic acid or cannabinerolic acid (the Z isomer of CBGA) to form CBCA. [3]

See also

Related Research Articles

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Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene, is one of the hundreds of cannabinoids found in the Cannabis plant, and is therefore a phytocannabinoid. It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBC and its derivatives are as abundant as cannabinols in cannabis. It is not scheduled by the Convention on Psychotropic Substances.

Olivetol Chemical compound

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Tetrahydrocannabinolic acid synthase

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12-Hydroxyheptadecatrienoic acid Chemical compound

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Cannabigerolic acid Chemical compound

Cannabigerolic acid (CBGA) is the acidic form of cannabigerol (CBG). It is a dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the Cannabis plant. It is a dihydroxybenzoic acid, a diterpenoid, a polyketide, a member of resorcinols and a phytocannabinoid. It derives from an olivetolic acid. It is a conjugate acid of a cannabigerolate.

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References

  1. ↑ "KNApSAcK Metabolite Information - C00053033". www.knapsackfamily.com.
  2. ↑ Shoyama Y, Fujita T, Yamauchi T, Nishioka I (June 1968). "Cannabichromenic acid, a genuine substance of cannabichromene". Chemical & Pharmaceutical Bulletin . 16 (6): 1157–8. doi:10.1248/cpb.16.1157. PMID   5706836.
  3. ↑ Morimoto S, Komatsu K, Taura F, Shoyama Y (November 1998). "Purification and characterization of cannabichromenic acid synthase from Cannabis sativa". Phytochemistry . 49 (6): 1525–9. doi:10.1016/s0031-9422(98)00278-7. PMID   9862135.
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