2415-24-9

Basic information

• Product Name: Catalpol
• Synonyms: CATALPOL;CATAPOL;,6-beta,6a-alpha))-;beta-d-glucopyranoside,1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl);catalpinoside;de(p-hydroxybenzoyl)catalposide;des-p-hydroxybenzoyl-catalposid;oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl,(1as-(1a-alpha,1b-beta,2-beta,5a-beta
• CAS NO: 2415-24-9
• Molecular Formula: C₁₅H₂₂O₁₀
• Molecular Weight: 362.33
• EINECS: 219-324-0
• Product Categories: Iridoids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 2415-24-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 203-205°C
• Boiling Point: 675.6 °C at 760 mmHg
• Flash Point: 362.4 °C
• Appearance: powder
• Density: 1.72 g/cm³
• Vapor Pressure: 3.77E-21mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: ?20°C
• Solubility: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• PKA: 12.79±0.70(Predicted)
• CAS DataBase Reference: Catalpol(CAS DataBase Reference)
• NIST Chemistry Reference: Catalpol(2415-24-9)
• EPA Substance Registry System: Catalpol(2415-24-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: LZ5776816
• Hazardous Substances Data: 2415-24-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Catalpol is used as a pharmaceutical agent for its diverse biological activities, including anti-apoptotic, pro-angiogenic, and radioprotective properties. It is particularly useful in the development of treatments for conditions involving cell damage, such as those caused by ionizing radiation or other harmful agents.
Used in Neuropathic Pain Management:
Catalpol is used as an analgesic agent for alleviating neuropathic pain. Its effectiveness in reducing pain and improving the quality of life for patients suffering from neuropathic pain conditions makes it a valuable compound in the field of pain management.
Used in Radioprotective Applications:
Catalpol is used as a radioprotective agent to reduce the harmful effects of ionizing radiation on cells and tissues. Its ability to protect against radiation-induced apoptosis and improve cell viability makes it a promising candidate for use in medical and industrial settings where exposure to radiation is a concern.
Used in Angiogenesis Promotion:
Catalpol is used as a pro-angiogenic agent to promote the formation of new blood vessels in the body. This property makes it a potential therapeutic option for conditions where improved blood flow and oxygen supply are needed, such as in the treatment of stroke or other ischemic conditions.
Chemical Properties:
Catalpol is a light brown powder, which is a characteristic of its chemical structure as an iridoid glucoside.

InChI:InChI=1/C15H22O10/c16-3-6-9(19)10(20)11(21)14(23-6)24-13-7-5(1-2-22-13)8(18)12-15(7,4-17)25-12/h1-2,5-14,16-21H,3-4H2

Upstream product

• 147714-71-4 6-O-[(E)-3,4-dimethoxycinnamoyl]catalpol 
• 1374308-81-2 (1aS,1bS,5aR,6S,6aS)-1a-{[(3,4-dimethoxybenzoyl)oxy]methyl}-1a,1b,2,5a,6,6a-hexahydro-6-methoxyoxireno[4,5]cyclopenta[1,2-c]pyran-2-yl β-D-glucopyranoside 
• 50932-20-2 6-O-(3,4-dihydroxybenzoyl)catalpol 
• 75598-56-0 2',3',4',6',10-Pentaacetyl-6-(4-acetylvanilloyl)catalpol 
• 81720-06-1 rehmannioside B 
• 6910-20-9 2',3',4',6,6',10-Hexaacetylcatalpol 

Downstream Products

• 87946-74-5 (-)-specionin 
• 113466-55-0 4-Benzyloxy-benzoic acid (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester 
• 113466-54-9 (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-ol 
• 89255-33-4 (1aS,1bS,2R,5aR,6S,6aS)-1a-Hydroxymethyl-1a,1b,2,5a,6,6a-hexahydro-1,3-dioxa-cyclopropa[a]indene-2,6-diol 
• 103744-70-3 C₂₅H₂₄O₈ 
• 85249-05-4 (1S,2S,6R,7R)-(-)-2-(Benzylthio)-7-hydroxy-3-oxabicyclo<4.3.0>nonan-9-on 
• 97119-20-5 Toluene-4-sulfonic acid (1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1b,5a,6,6a-tetrahydro-2H-1,3-dioxa-cyclopropa[a]inden-1a-ylmethyl ester 
• 105562-53-6 2',3',4',6-Tetraacetyl-6',10-bis(triphenylmethyl)catalpol 

Relevant articles and documents

10-O-acylated iridoid glucosides from leaves of Premna subscandens

From the 1-butanol-soluble fraction of a methanol extract of leaves of Premna subscandens, collected on Ishigaki Island, Okinawa, ten 10-O-acylated derivatives of catalpol and asystasioside E were isolated. The structures of nine new compounds were elucidated by spectroscopic methods and by chemical conversion.

Chlorinated iridoid glucosides from Veronica longifolia and their antioxidant activity

From Veronica longifolia were isolated three chlorinated iridoid glucosides, namely, asystasioside E (6) and its 6-O-esters 6a and 6b, named longifoliosides A and B, respectively. The structures of 6a and 6b were proved by analysis of their spectroscopic data and by conversion to the catalpol ester verproside (5a) or to catalpol (5), respectively. The configuration of the previously known vanilloyl analogue, urphoside B, was shown to be the 6β-epimer (6c) of the structure originally reported. Longifoliosides A (6a) and B (6b) were found to exhibit radical-scavenging activity against nitric oxide, superoxide, and 2,2-diphenyl-1-picrylhydrazyl radicals.

Isolation, semi-synthesis, docking-based prediction, and bioassay-based activity ofDolichandrone spathaceairidoids: new catalpol derivatives as glucosidase inhibitors

Dolichandrone spathaceairidoids are promising anti-diabetic inhibitors towards α-glucosidase protein (PDB-) and oligo-1,6-glucosidase protein. Five catalpol iridoids(1,2,10,13,14)were isolated from mangrove plantD. spathacea, and their derivatives (3,4,5,6,7,8,9,11,12,15) were obtained from reduction, acetylation,O-alkylation, acetonisation, or hydrolysation starting from naturally isolated compounds. They were identified by spectral methods such as IR, MS, and 1D and 2D NMR. Their glucosidase-related (inhibitability and physiological compatibility were predicted by molecular docking simulation and prescreened based on Lipinski's rule of five. Experimental α-glucosidase inhibition of1-15was evaluated using enzyme assays. Compounds3,4,5,6, and9are new iridoid derivatives, introduced to the literature for the first time, while all fifteen compounds1-15are studied for molecular docking for the first time. Regarding protein, the five strongest predicted inhibitors assemble in the order2>10>1>9>14. In respect to, the corresponding order is14>2>10>5>1=9. Lipinski's criteria suggest10as the candidate with the most potential for oral administration. Thein vitrobioassay revealed that compound10is the most effective inhibitor with a respective IC50value of 0.05 μM, in the order10>2>14>13>1. The computational and experimental results show good consistency. The study opens an alternative approach for diabetes treatment based on inhibitability of natural and semi-synthesised catalpol iridoid derivatives towards carbohydrate-hydrolases.

Eremosides A-C, new iridoid glucosides from Eremostachys loasifolia

Eremosides A-C (1 - 3), three new iridoid glucosides, were isolated from the AcOEt-soluble fraction of the EtOH extract of the whole plant of Eremostachys loasifolia, along with buddlejoside B (4), 10-O-benzoylcatalpol (5), and pakiside A (6) reported for the first time from this species. The structures of these compounds were elucidated by spectroscopic data including 2D-NMR, FAB-MS, ESI-MS, as well as by acid and basic hydrolyses.

New glycosidic constituents of abutilon Pakistanicum

Pakisides A and B (1 and 2, resp.), new catalpol-type iridoid glycosides, and a new glycoside, 3, of scutellarein have been isolated from the AcOEt-soluble fraction of the whole plant of Abutilon pakistanicum, along with buddlejoside and lapachol. The structures of new compounds were elucidated by spectroscopic techniques including 1H-and 13C-NMR (DEPT), and 2D-NMR experiments. Copyright 2010 Verlag Helvetica Chimica Acta AG, Zuerich, Switzerland.

PHARMACEUTICAL COMPOSITION COMPRISING AN EXTRACT OF PSEUDOLYSIMACHION LONGIFOLIUM AND THE CATALPOL DERIVATIVES ISOLATED THEREFROM HAVING ANTIINFLAMMATORY, ANTIALLERGIC AND ANTIASTHMATIC ACTIVITY

The present invention relates to a composition comprising an extract of Pseudolysimachion genus plant, and the catalpol derivatives isolated therefrom having anti-inflammatory, antiallergic and anti-asthmatic activity. The extractof Pseudolysimachion genus plantand the catalpol derivatives isolated therefrom shows potent suppressing effect on elevated IgE, IL-4 and IL- 13 levels and eosinophilia in the plasma and BALF, and mucus overproduction in the lung tissues in an OVA-induced asthmatic mouse model. Therefore, it can be used as the therapeutics or functional health food for treating and preventing inflammatory, allergic and asthmatic disease.

New iridoid glucoside from Picrorhiza kurroa Royle ex Benth

Picrorhiza kurroa Royle ex Benth, commonly known as kutki is used as a crude drug reported in Indian pharmacopoeia. Acetyl derivative of a new iridoid glucoside, picroside V (6-m-methoxybenzoyl catalpol) along with three known iridoid glucosides picroside I, picroside II and catalpol have been isolated from the roots of Picrorhiza kurroa Royle ex Benth.

Megastigmane, benzyl and phenethyl alcohol glycosides, and 4,4'- dimethoxy-β-truxinic acid catalpol diester from the leaves of Premna subscandens Merr.

Extensive isolation work on the n-BuOH-soluble fraction obtained from the leaves of Premna subscandens, collected on Ishigaki island, Okinawa, afforded six compounds. Two were identified as megastigmane glucosides, 7- (3,5-dihydroxy-1,1,5-trimethylcyclohexylidene)-9-methylprop-8-enyl 9-O-β-D- glucopyranoside and 3-hydroxy-5,6-epoxy-β-ionol 9-O-β-D-glucopyranoside. The structures of the remaining four new compounds were elucidated to be a 2'-O-β-D-apiofuranosyl derivative of 3-hydroxy-5,6-epoxy-β-ionol 9-O-β-D- glucopyranoside, named premnaionoside, benzyl alcohol β-D-(2'-O-β-D- xylopyranosyl)glucopyranoside, phenethyl alcohol β-D-(2'-O-β-D- glucopyranosyl)glucopyranoside, and 4,4'-dimethoxy-β-truxinic acid catalpol diester by spectroscopic analyses.