Olivetolic acid

Structural formula
General
Surname	Olivetolic acid
other names	4-hydroxy-6- n -pentylsalicylic acid
Molecular formula	C 12 H 16 O 4
External identifiers / databases
PubChem	2826719
ChemSpider	2104822
Wikidata	Q3604545
properties
Molar mass	224.25 g mol −1
Melting point	148-149 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Olivetolsäure , also 4-hydroxy-6- n -pentylsalicylsäure , the carboxylic acid - derivative of olivetol . It is a meroterpenoid that serves as the biogenetic precursor of various derivatives of dibenzopyran - so-called cannabinoids . Cannabigerolic acid is formed by enzymatic condensation from the two precursors geranyl pyrophosphate and olivetolic acid , which is then enzymatically rearranged into tetrahydrocannabinolic acid . Olivetolic acid itself is probably synthesized in a similar way to orsellic acid , starting from a tetraketide that is formed from caproic acid and three acetate units. Olivetolic acid can also be artificially represented. Olivetolic acid occurs naturally in the fungus Cetrelia sanguinea and has a monoclinic crystal structure with the space group P 2 ₁ / n (space group no. 14, position 2) . Template: room group / 14.2

It differs from orsellic acid in the length of the alkyl side chain. The olivetol is produced by decarboxylation .

Individual evidence

↑ MP Polovinka; NI Komarova; DV Korchagina; DN Sokolov; OA Luzina; NG Vlasenko; AA Malyuga; EV Romanova; NF Salakhutdinov: Secondary metabolites of the lichen Cladonia stellaris in Chemistry of Natural Compounds 48 (2012) 392-395, doi : 10.1007 / s10600-012-0259-4 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b Albert Gossauer: Structure and reactivity of biomolecules an introduction to organic chemistry . John Wiley & Sons, 2006, ISBN 3-906390-29-2 , pp. 420 ( limited preview in Google Book search).
↑ J. Jung, MR Meyer, H. H. Maurer, C. Neusüß, W. Weinmann, V. Auwärter: Studies on the metabolism of the Δ9-tetrahydrocannabinol precursor Δ9-tetrahydrocannabinolic acid A (Δ9-THCA-A) in rat using LC- MS / MS, LC-QTOF MS and GC-MS techniques . In: Journal of Mass Spectrometry . tape 44 , no. 10 , 2009, p. 1423-1433 , doi : 10.1002 / jms.1624 .
↑ Breitmaier, Eberhard et al .: Organic Chemistry, 2012, Chap. 45: Biosynthesis of Natural Products, 45.6 Polyketide, doi : 10.1055 / b-0034-44145 .
↑ Comprehensive Natural Products II: Chemistry and Biology . Newnes, 2010, ISBN 0-08-045382-1 , pp. 192 ( limited preview in Google Book search).
↑ A. Chittiboyina, IA Khan: Short Synthesis of Olivetolic Acid via Directed ortho-Metalation (DoM). In: Planta Medica . 78, 2012, doi: 10.1055 / s-0032-1307550 .
↑ Friardi Ismed, Aulia Farhan, Amri Bakhtiar, Erizal Zaini, Yuda Prasetya Nugraha, Okky Dwichandra Putra, Hidehiro Uekusa: Crystal structure of olivetolic acid: a natural product from (Schaer.). In: Acta Crystallographica Section E Crystallographic Communications. 72, 2016, p. 1587, doi: 10.1107 / S2056989016016273 .

[1] MP Polovinka; NI Komarova; DV Korchagina; DN Sokolov; OA Luzina; NG Vlasenko; AA Malyuga; EV Romanova; NF Salakhutdinov: Secondary metabolites of the lichen Cladonia stellaris in Chemistry of Natural Compounds 48 (2012) 392-395, doi : 10.1007 / s10600-012-0259-4 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Albert_Gossauer-3] Albert Gossauer: Structure and reactivity of biomolecules an introduction to organic chemistry . John Wiley & Sons, 2006, ISBN 3-906390-29-2 , pp. 420 ( limited preview in Google Book search).

[4] J. Jung, MR Meyer, H. H. Maurer, C. Neusüß, W. Weinmann, V. Auwärter: Studies on the metabolism of the Δ9-tetrahydrocannabinol precursor Δ9-tetrahydrocannabinolic acid A (Δ9-THCA-A) in rat using LC- MS / MS, LC-QTOF MS and GC-MS techniques . In: Journal of Mass Spectrometry . tape 44 , no. 10 , 2009, p. 1423-1433 , doi : 10.1002 / jms.1624 .

[thieme-connect.de-5] Breitmaier, Eberhard et al .: Organic Chemistry, 2012, Chap. 45: Biosynthesis of Natural Products, 45.6 Polyketide, doi : 10.1055 / b-0034-44145 .

[6] Comprehensive Natural Products II: Chemistry and Biology . Newnes, 2010, ISBN 0-08-045382-1 , pp. 192 ( limited preview in Google Book search).

[7] A. Chittiboyina, IA Khan: Short Synthesis of Olivetolic Acid via Directed ortho-Metalation (DoM). In: Planta Medica . 78, 2012, doi: 10.1055 / s-0032-1307550 .

[8] Friardi Ismed, Aulia Farhan, Amri Bakhtiar, Erizal Zaini, Yuda Prasetya Nugraha, Okky Dwichandra Putra, Hidehiro Uekusa: Crystal structure of olivetolic acid: a natural product from (Schaer.). In: Acta Crystallographica Section E Crystallographic Communications. 72, 2016, p. 1587, doi: 10.1107 / S2056989016016273 .