Structure Database (LMSD)

Common Name
Cannabinolic acid
Systematic Name
1-hydroxy-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-2-carboxylic acid
Synonyms
  • CBNA
LM ID
LMPK13120007
Formula
Exact Mass
Calculate m/z
354.18311
Status
Curated

Classification

Biological Context

Cannabinolic acid is an analytical reference standard that is structurally similar to known phytocannabinoids.1 Cannabinolic acid has been found in Cannabis and is an oxidative product of Δ9-THCA (THCA-A).1,2 This product is intended for research and forensic applications.

This information has been provided by Cayman Chemical

References

1. Moreno, T., Dyer, P., and Tallon, S. Cannabinoid decarboxylation: A comparative kinetic study. Ind. Eng. Chem. Res. 59(46), 20307-20315 (2020).
2. Basas-Jaumandreu, J., and de Las Heras, F.X.C. GC-MS metabolite profile and identification of unusual homologous cannabinoids in high potency Cannabis sativa. Planta Med. 86(5), 338-347 (2020).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Cannabis sativa (#3483)
Magnoliopsida (#3398)
Hashish. IV. The isolation and structure of cannabinolic cannabidiolic and cannabigerolic acids.,
Tetrahedron, 1965
Pubmed ID: 5879350

String Representations

InChiKey (Click to copy)
KXKOBIRSQLNUPS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C22H26O4/c1-5-6-7-8-14-12-17-19(20(23)18(14)21(24)25)15-11-13(2)9-10-16(15)22(3,4)26-17/h9-12,23H,5-8H2,1-4H3,(H,24,25)
SMILES (Click to copy)
C12=C(C(C)(OC3C=C(C(C(O)=O)=C(O)C=31)CCCCC)C)C=CC(C)=C2

Other Databases

PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 3
Aromatic Rings 2
Rotatable Bonds 5
Van der Waals Molecular Volume 346.96
Topological Polar Surface Area 68.83
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 5.43
Molar Refractivity 102.12

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Created at
31st Jul 2024
Updated at
31st Jul 2024