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Cannabidiolic acid

Cannabidiolic acid (CBDA), is a cannabinoid found in cannabis plants.[1] It is most abundant in the glandular trichomes on the female seedless flowers or more accurately infructescence often colloquially referred to as buds.[2] CBDA is the chemical precursor to cannabidiol (CBD). Through the process of decarboxylation cannabidiol is derived via a loss of a carbon and two oxygen atoms from the 1 position of the benzoic acid ring. Cannabinoids are a class of compounds that are essentially unique to the cannabis genus.  Both marijuana and hemp belong to this genus.

Cannabidiolic acid
Names
Preferred IUPAC name
(1′R,2′R)-2,6-Dihydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro[1,1′-biphenyl]-3-carboxylic acid
Identifiers
  • 1244-58-2
3D model (JSmol)
  • Interactive image
3DMet
  • B04205
ChEBI
  • CHEBI:3359
ChEMBL
  • ChEMBL498672
ChemSpider
  • 141099
KEGG
  • C10784
  • 160570
UNII
  • FJX8O3OJCD
  • DTXSID80154318
  • InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1
    Key: WVOLTBSCXRRQFR-DLBZAZTESA-N
  • CCCCCC1=CC(=C(C(=C1C(=O)O)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)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).

Chemical composition edit

Cannabidiolic acid is biosynthesized by Cannabidiolic acid synthase from the conjugation of olivetolic acid and cannabigerolic acid.[3] CBDA is not produced by man, but it is naturally occurs in hemp.  It is a raw compound which is found in the flowering buds of the female cannabis plant.[4]

References edit

  1. ^ Takeda, Shuso (2013). "[Medicinal chemistry and pharmacology focused on cannabidiol, a major component of the fiber-type cannabis]". Yakugaku Zasshi: Journal of the Pharmaceutical Society of Japan. 133 (10): 1093–1101. doi:10.1248/yakushi.13-00196. ISSN 1347-5231. PMID 24088353.
  2. ^ Livingston, Samuel J.; Quilichini, Teagen D.; Booth, Judith K.; Wong, Darren C. J.; Rensing, Kim H.; Laflamme‐Yonkman, Jessica; Castellarin, Simone D.; Bohlmann, Joerg; Page, Jonathan E.; Samuels, A. Lacey (2020). "Cannabis glandular trichomes alter morphology and metabolite content during flower maturation". The Plant Journal. 101 (1): 37–56. doi:10.1111/tpj.14516. ISSN 1365-313X. PMID 31469934.
  3. ^ PubChem. "Cannabidiolic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-12-23.
  4. ^ Nadel, David (2020-10-02). "Hemp Compound Spotlight: CBDA". Pure CBD Now. Retrieved 2022-12-18.

cannabidiolic, acid, cbda, cannabinoid, found, cannabis, plants, most, abundant, glandular, trichomes, female, seedless, flowers, more, accurately, infructescence, often, colloquially, referred, buds, cbda, chemical, precursor, cannabidiol, through, process, d. Cannabidiolic acid CBDA is a cannabinoid found in cannabis plants 1 It is most abundant in the glandular trichomes on the female seedless flowers or more accurately infructescence often colloquially referred to as buds 2 CBDA is the chemical precursor to cannabidiol CBD Through the process of decarboxylation cannabidiol is derived via a loss of a carbon and two oxygen atoms from the 1 position of the benzoic acid ring Cannabinoids are a class of compounds that are essentially unique to the cannabis genus Both marijuana and hemp belong to this genus Cannabidiolic acid NamesPreferred IUPAC name 1 R 2 R 2 6 Dihydroxy 5 methyl 4 pentyl 2 prop 1 en 2 yl 1 2 3 4 tetrahydro 1 1 biphenyl 3 carboxylic acidIdentifiersCAS Number 1244 58 23D model JSmol Interactive image3DMet B04205ChEBI CHEBI 3359ChEMBL ChEMBL498672ChemSpider 141099KEGG C10784PubChem CID 160570UNII FJX8O3OJCDCompTox Dashboard EPA DTXSID80154318InChI InChI 1S C22H30O4 c1 5 6 7 8 15 12 18 23 20 21 24 19 15 22 25 26 17 11 14 4 9 10 16 17 13 2 3 h11 12 16 17 23 24H 2 5 10H2 1 3 4H3 H 25 26 t16 17 m0 s1Key WVOLTBSCXRRQFR DLBZAZTESA NSMILES CCCCCC1 CC C C C1C O O O C H 2C C CC C H 2C C C C OPropertiesChemical formula C 22H 30O 4Molar mass 358 478 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesChemical composition editCannabidiolic acid is biosynthesized by Cannabidiolic acid synthase from the conjugation of olivetolic acid and cannabigerolic acid 3 CBDA is not produced by man but it is naturally occurs in hemp It is a raw compound which is found in the flowering buds of the female cannabis plant 4 References edit Takeda Shuso 2013 Medicinal chemistry and pharmacology focused on cannabidiol a major component of the fiber type cannabis Yakugaku Zasshi Journal of the Pharmaceutical Society of Japan 133 10 1093 1101 doi 10 1248 yakushi 13 00196 ISSN 1347 5231 PMID 24088353 Livingston Samuel J Quilichini Teagen D Booth Judith K Wong Darren C J Rensing Kim H Laflamme Yonkman Jessica Castellarin Simone D Bohlmann Joerg Page Jonathan E Samuels A Lacey 2020 Cannabis glandular trichomes alter morphology and metabolite content during flower maturation The Plant Journal 101 1 37 56 doi 10 1111 tpj 14516 ISSN 1365 313X PMID 31469934 PubChem Cannabidiolic acid pubchem ncbi nlm nih gov Retrieved 2019 12 23 Nadel David 2020 10 02 Hemp Compound Spotlight CBDA Pure CBD Now Retrieved 2022 12 18 Retrieved from https en wikipedia org w index php title Cannabidiolic acid amp oldid 1148053869, wikipedia, wiki, book, books, library,

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