Catalpol

Structural formula
General
Surname	Catalpol
other names	Catalpinoside
Molecular formula	C 15 H 22 O 10
Brief description	light brown solid
External identifiers / databases
CAS number 2415-24-9 EC number 219-324-0 ECHA InfoCard 100,017,568 PubChem 91520 ChemSpider 82641 Wikidata Q1050267
properties
Molar mass	362.33 g mol −1
Physical state	firmly
Melting point	202-205 ° C
solubility	soluble in water
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-264-280-304 + 340 + 312-337 + 313-403 + 233
Toxicological data	> 2,500 mg kg −1 ( LD 50 ,  mouse ,  iv ) > 10 g kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Catalpol is a common phytochemical from the group of iridoids . It is a glycoside of its aglycone with the monosaccharide glucose . Like other monoterpenes , the aglycone is synthesized from two isoprene units with five carbon atoms each in the plant. In contrast to the C10 basic body of the iridoids, the catalpol basic structure has only nine carbon atoms, since a methyl group is oxidized to a carboxylic acid group during biosynthesis and then split off as carbon dioxide . Catalpol is similar in structure to aucubin ; however, it has an epoxy ring instead of a double bond .

Catalpol occurs mainly as an ester of various aromatic carboxylic acids. The esters form on the primary hydroxy group (R ¹ ), e.g. B. Scutellariosid I ( Globularin , R ¹ = cinnamoyl) or on the secondary hydroxyl group (R ² ), z. B. catalposid (R ² = 4-hydroxybenzoyl) or on the hydroxy group at C-6 of the glucose, z. B. Picroside I (cinnamoyl at C6 of glucose).

Trumpet tree ( Catalpa bignonioides ) contains Catalpol.

Catalpol was isolated from the trumpet tree Catalpa bignonioides ( Bignoniaceae ), which is native to North America and East Asia , and is the most abundant iridoid glucoside along with aucubin .

literature

• R. Hansel, O. Sticher: Pharmacognosie, Phytopharmazie . 8th edition. Springer publishing house. Berlin 2007. ISBN 3-540-34256-7

Individual evidence

1. ↑ ^{a b c} Datasheet Catapol at Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).
2. ↑ ^{a b c} Entry on Catalpol. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.
3. ↑ Cayman Chemical: Catalpol (CAS 2415-24-9) | Cayman Chemical , accessed June 29, 2019
4. ↑ ^{a b} Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology , 1968, Vol. 64, p. 93.
5. ↑ ^{a b} Entry on Catalpol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
6. ↑ External identifiers or database links for Catalposid : CAS number: 6736-85-2, EC number: 229-789-1, ECHA InfoCard: 100.027.082 , PubChem : 53297355 , ChemSpider : 30791175 , Wikidata : Q27106093 .
7. ↑ External identifiers or database links for Picrosid I : CAS number: 27409-30-9, EC number: 248-445-1, ECHA InfoCard: 100.044.027 , PubChem : 6440892 , ChemSpider : 23089604 , Wikidata : Q72499472 .