| Identification | Back Directory | [Name]
Catalpol | [CAS]
2415-24-9 | [Synonyms]
CATAPOL
CATALPOL
catalpinoside
Catapol ,>=98%
Catalpol，Catalnol
CATALPOL WITH HPLC
Catalpol 2415-24-9
,6-beta,6a-alpha))-
Catalpol, ≥97%(HPLC)
Digitalis purpurea L
de(p-hydroxybenzoyl)catalposide
des-p-hydroxybenzoyl-catalposid
β-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-
oxireno(4,5)cyclopenta(1,2-c)pyran-2-yl,(1as-(1a-alpha,1b-beta,2-beta,5a-beta
beta-d-glucopyranoside,1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)
1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl
[(1aS)-1a,1bα,2,5aα,6,6aβ-Hexahydro-6α-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2α-yl]β-D-glucopyranoside
(1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-Hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl-β-D-glucopyranoside
β-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl
.beta.-D-Glucopyranoside, (1aS,1bS,2S,5aR,6S,6aS)-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno4,5cyclopenta1,2-cpyran-2-yl
(1AS-(1aα,1bβ,2β,5aβ,6β,6aα-))1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxyMethyl)oxireno(4,5)cyclopenta(1,2-c)-pyran-2-yl-beta-D-glucopyranoside
[1aS-(1aalpha,1bbeta,2beta,5abeta,6beta,6a.alpha.)]-1a,1b,2,5a,6,6a-hexahydro-6-hydroxy-1a-(hydroxymethyl)oxireno[4,5]cyclopenta[1,2-c]pyran-2-yl-beta-D-glucopyranoside
(2S,3R,4S,5S,6R)-2-[[(1aS,1bS,2S,5aR,6S,6aS)-6-hydroxy-1a-(hydroxymethyl)-2,5a,6,6a-tetrahydro-1bH-oxireno[5,6]cyclopenta[1,3-c]pyran-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
(3R,4S,5S,6R)-2-(((1aS,1bS,2S,5aR,6S,6aS)-6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
(2S,3R,4S,5S,6R)-2-(((1aS,1bS,2S,5aR,6S,6aS)-6-Hydroxy-1a-(hydroxymethyl)-1a,1b,2,5a,6,6a-hexahydrooxireno[2',3':4,5]cyclopenta[1,2-c]pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | [EINECS(EC#)]
219-324-0 | [Molecular Formula]
C15H22O10 | [MDL Number]
MFCD00066264 | [MOL File]
2415-24-9.mol | [Molecular Weight]
362.33 |
| Chemical Properties | Back Directory | [Melting point ]
203-205°C | [Boiling point ]
675.6±55.0 °C(Predicted) | [density ]
1.72±0.1 g/cm3(Predicted) | [storage temp. ]
?20°C | [solubility ]
DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly) | [form ]
Solid | [pka]
12.79±0.70(Predicted) | [color ]
White to Off-White | [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/t5-,6-,7-,8+,9-,10+,11-,12+,13+,14+,15-/s3 | [InChIKey]
LHDWRKICQLTVDL-CLLMHHLUSA-N | [SMILES]
C([C@]12O[C@H]1[C@@H](O)[C@]1([H])C=CO[C@@H](O[C@@]3([H])[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@]21[H])O |&1:1,3,4,6,11,13,15,16,18,20,25,r| | [LogP]
-4.609 (est) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3 | [RTECS ]
LZ5776816 | [HS Code ]
29389090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | [Toxicity]
mouse,LD,intravenous,> 2500mg/kg (2500mg/kg),Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 93, 1968. |
| Hazard Information | Back Directory | [Description]
Catalpol is an iridoid glycoside that has been isolated from R. glutinosa and has diverse biological activities, including anti-apoptotic, pro-angiogenic, and radioprotective properties.1 It protects against mitochondrial pathway-dependent apoptosis in PC12 rat adrenal pheochromocytoma cells and H9c2 rat embryonic ventricular myocardial cells when used at a concentration of 10 μM.2,3 Catalpol pretreatment reduces apoptosis and improves viability in AHH-1 human lymphocyte cells exposed to ionizing radiation and reduces intestinal damage induced by radiation in mice when used at concentrations and doses ranging from of 25 to 100 μg/ml and 25 to 100 mg/kg, respectively.4 In a rat model of stroke, catalpol (5 mg/kg, i.p.) increases the expression of erythropoietin and VEGF and improves angiogenesis in the brain.5 | [Chemical Properties]
Light brown powder | [Uses]
Catapol is an iridoid glucoside that has been shown to alleviate neuropathic pain. | [Definition]
ChEBI: Catalpol is an organic molecular entity. It has a role as a metabolite. | [in vivo]
Catalpol (25-100?mg/kg; intraperitoneal injection; once) treatment clearly reduces blood urea nitrogen, serum creatinine levels and the expression of KIM-1 in renal ischemia/reperfusion-injury (IRI) mice. Catalpol markedly reduces the expression of PI3K, Akt and eNOS levels, and suppresses the TNF-α, IL-1β, IL-6 and IL-10 activities[1]. | Animal Model: | C57BL/6 mice treated with renal ischemia/reperfusion surgery[1] | | Dosage: | 25 mg/kg, 50 mg/kg and 100?mg/kg | | Administration: | Intraperitoneal injection; once | | Result: | Clearly reduced blood urea nitrogen, serum creatinine levels and the expression of KIM-1 in renal IRI mice.
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| [References]
[1] YANJIE WANG. Simultaneous Determination of Catalpol, Aucubin, and Geniposidic Acid in Different Developmental Stages of Rehmannia glutinosa Leaves by High Performance Liquid Chromatography.[J]. Journal of Analytical Methods in Chemistry, 2016, 2016: 4956589. DOI: 10.1155/2016/4956589
[2] WENNA CHEN. Neuroprotective activities of catalpol against CaMKII-dependent apoptosis induced by LPS in PC12 cells[J]. British Journal of Pharmacology, 2013, 169 5: 1140-1152. DOI: 10.1111/bph.12200
[3] LING-AI HU. Catalpol inhibits apoptosis in hydrogen peroxide-induced cardiac myocytes through a mitochondrial-dependent caspase pathway.[J]. Bioscience Reports, 2016, 36 3. DOI: 10.1042/bsr20160132
[4] CHENGJIE CHEN. Radio-protective effect of catalpol in cultured cells and mice.[J]. Journal of Radiation Research, 2013, 54 1: 76-82. DOI: 10.1093/jrr/rrs080
[5] HUI-FENG ZHU. Catalpol increases brain angiogenesis and up-regulates VEGF and EPO in the rat after permanent middle cerebral artery occlusion.[J]. International Journal of Biological Sciences, 2010, 6 5: 443-453. DOI: 10.7150/ijbs.6.443 |
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