Cannabichromenic acid

Cannabichromenic acid
Names
	IUPAC name 5-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromene-6-carboxylic acid
	Other names CBCA; (+)-Cannabichromenic acid;
Identifiers
CAS Number	(±): 185505-15-1; (+): 20408-52-0;
3D model (JSmol)	(±): Interactive image;
ChEBI	(±): CHEBI:167557;
ChEMBL	(±): ChEMBL4594109;
ChemSpider	(±): 2341420;
PubChem CID	(±): 3084339;
UNII	(±): NNW8UMP980;
CompTox Dashboard (EPA)	(±): DTXSID301336859 DTXSID80942575, DTXSID301336859 ;
	InChI 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;
	SMILES (±): CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1C(=O)O)O;
Properties
Chemical formula	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

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

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]

References

^ "KNApSAcK Metabolite Information - C00053033". www.knapsackfamily.com.
^ 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.
^ 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.

Notes

This article is a direct transclusion of the Wikipedia article and therefore may not meet the same editing standards as LIMSwiki.

[1] "KNApSAcK Metabolite Information - C00053033". www.knapsackfamily.com.

[pmid5706836-2] 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.

[pmid9862135-3] 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.

[1]

[2]

[3]

Cannabichromenic acid

Biosynthesis

See also

References

Notes

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Names

IUPAC name 5-Hydroxy-2-methyl-2-(4-methylpent-3-enyl)-7-pentylchromene-6-carboxylic acid
Other names CBCA (+)-Cannabichromenic acid
Identifiers
CAS Number	(±): 185505-15-1 (+): 20408-52-0^[1]
3D model (JSmol)	(±): Interactive image
ChEBI	(±): CHEBI:167557
ChEMBL	(±): ChEMBL4594109
ChemSpider	(±): 2341420
PubChem CID	(±): 3084339
UNII	(±): NNW8UMP980
CompTox Dashboard (EPA)	(±): DTXSID301336859 DTXSID80942575, DTXSID301336859
InChI 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
SMILES (±): CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1C(=O)O)O
Properties
Chemical formula	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