6926-08-5

Basic information

• Product Name: Harpagide
• Synonyms: HARPAGIDE;EINECS 230-050-0;(1S-(1a,4aa,5a,7a,7a))-1,4a,5,6,7,7a-Hexahydro-4a,5,7-trihydroxy-7-methylcyclopenta[c]pyran-1-yl beta-D-glucopyranoside;1,4a,5,6,7,7a-hexahydro-4a,5,7-trihydroxy-7-methylcyclopenta[c]pyran-1-yl;β-D-Glucopyranoside, (1S,4aS,5R,7S,7aR)-;(1S)-1,4a,5,6,7,7aα-Hexahydro-4aα,5α,7α-trihydroxy-7-methylcyclopenta[c]pyran-1-yl β-D-glucopyranoside;[1S-(1α,4aα,5α,7α,7aα)]-1,4a,5,6,7,7a-hexahydro-4a,5,7-trihydroxy-7-methylcyclopenta[c]pyran-1-yl β-D-glucopyranoside;(1S-(1alpha,4Aalpha,5alpha,7alpha,7aalpha))-1,4A,5,6,7,7A-hexahydro-4A,5,7-trihydroxy-7-methylcyclopenta(C)pyran-1-yl beta-D-glucopyranoside
• CAS NO: 6926-08-5
• Molecular Formula: C₁₅H₂₄O₁₀
• Molecular Weight: 364.35
• EINECS: 230-050-0
• Product Categories: reference substance;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 6926-08-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 637.1 °C at 760 mmHg
• Flash Point: 339.1 °C
• Appearance: /
• Density: 1.66 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: 2-8°C
• PKA: 12.10±0.70(Predicted)
• CAS DataBase Reference: Harpagide(CAS DataBase Reference)
• NIST Chemistry Reference: Harpagide(6926-08-5)
• EPA Substance Registry System: Harpagide(6926-08-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 6926-08-5(Hazardous Substances Data)

Usage

Uses

Harpagide is an iridoid glycoside along with Harpagoside (H105275) with the potential to be strong anti-inflammatory agents providing the bulk of the observed effects from their plant origins.

InChI:InChI=1/C15H24O10/c1-14(21)4-7(17)15(22)2-3-23-13(11(14)15)25-12-10(20)9(19)8(18)6(5-16)24-12/h2-3,6-13,16-22H,4-5H2,1H3/t6-,7-,8-,9+,10-,11?,12+,13+,14+,15-/m1/s1

Upstream product

• 19210-12-9 harpagoside 
• 133561-41-8 8-O-cis-cinnamoyl-6-O-β-D-glucosylharpagide 
• 20770-66-5 penta-O-acetylantirrhinoside 
• 20770-66-5 Pentaacetylantirrhinosid 
• 87686-74-6 8-O-4-hydroxycinnamoylharpagide 
• 19210-12-9 8-O-cis-cinnamoylharpagide 
• 133561-42-9 trans-6'-O-p-coumaroylharpagide 

Relevant articles and documents

Iridoids As Allelochemicals and DNA Polymerase Inhibitors

Growth inhibitory activities and nutritional indices of catalpol (1), 8-O-acetylharpagide (2), and harpagide (3) were determinated in larvae and adults of Tribolium castaneum, respectively. Compound 1 produced a series of allelochemical effects probably related with the DNA synthesis. This iridoid possessed the highest inhibitory activity against DNA polymerase. Molecular orbital calculations suggest that a π-π charge transfer recognition model could explain the action of iridioids toward nucleic acid synthesis.

Effect of an 8-Hydroxymethyl Substituent on the Base-Catalyced Ring Opening of 7,8-Epoxyiridoid Glucosides

Base-catalyzed ring opening of 7,8-epoxyiridoids has been found to be dependent on the substitution pattern at C-8.Epoxyiridoids 5, 6, and 10 (CH3-8) react in barium or sodium hydroxide solutions through a normal SN2 process, yielding the expected 7α,8β-diols while for iridoids 3 and 4 (CH2OH-8) the stereochemistry of the final diol function is reversed (7β,8α).This abnormal SN2 process is explained by a preliminary "epoxide migration" from carbons 7,8 to 8,10 followed by normal oxirane cleavage.Participation of the CH2OH-8 substituent in the cleavage reaction is proved by the behavior of the hexa-O-methyl derivative 3 which gives the normal 7α,8β-diol.Four new nonnatural iridoid glucosides (9, 11, 14, 16) are also described and spectroscopically (1H and 13C NMR) characterized.

IRIDOID GLUCOSIDES FROM ROGERIA ADENOPHYLLA

Three new harpagide derivatives have been isolated from the aerial parts of Rogeria adenophylla (Pedaliaceae).Their structures have been established as 8-O-cis-cinnamoylharpagide, 8-O-cis-cinnamoyl-6-O-β-D-glucosyl-harpagide and 6'-O-p-coumaroyl harpagide respectively, the p-coumaroyl moiety of the latter existing in either the trans or cis configuration.In addition, harpagide, harpagoside, 8-O-trans-p-coumaroylharpagide, procumbide and verbascoside have been isolated and identified.