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19210-12-9

19210-12-9 Structure

19210-12-9 Structure
IdentificationMore
[Name]

Harpagoside
[CAS]

19210-12-9
[Synonyms]

8'-CINNAMOYLHARPAGIDE
8-O-E CINNAMOYL HARPAGIDE
HARPAGOSIDE
Harpagosid
[1S-[1alpha,4aalpha,5alpha,7alpha(E),7aalpha]]-1,4a,5,6,7,7a-hexahydro-4a,5-dihydroxy-7-methyl-7-[(allyl-1-oxo-3-phenyl)oxy]cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside
Harpogoside
HARPAGOSIDE hplc
[(1S,4aS,5R,7S,7aS)-4a,5-Dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-phenylprop-2-enoate
HARPAGOSIDE WITH HPLC
7,7a-hexahydro-4a,5-dihydroxy-7-methyl-7-[[(2E)-1-oxo-3-phenyl-2-propen-1-yl]oxy]cyclopenta[c]pyran-1-yl
β-D-Glucopyranoside, (1S,4aS,5R,7S,7aS)-1,4a,5,6
[(1S)-1,4a,5,6,7,7aα-Hexahydro-4aα,5α-dihydroxy-7-methyl-7α-[[(E)-1-oxo-3-phenyl-2-propenyl]oxy]cyclopenta[c]pyran-1α-yl]β-D-glucopyranoside
[EINECS(EC#)]

242-881-6
[Molecular Formula]

C24H30O11
[MDL Number]

MFCD00017415
[Molecular Weight]

494.49
[MOL File]

19210-12-9.mol
Chemical PropertiesBack Directory
[Melting point ]

120°C (dec.)
[Boiling point ]

720.7±60.0 °C(Predicted)
[density ]

1.52±0.1 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)
[form ]

neat
[pka]

11.70±0.70(Predicted)
[color ]

White to Light Yellow
[Optical Rotation]

[α]/D -50 to -30°
[Stability:]

Hygroscopic
[Cosmetics Ingredients Functions]

SKIN CONDITIONING
[InChIKey]

KVRQGMOSZKPBNS-FMHLWDFHSA-N
[SMILES]

O[C@@]12C=CO[C@@H](O[C@@]3([H])[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@]1([H])[C@@](C)(OC(=O)/C=C/C1C=CC=CC=1)C[C@H]2O |&1:1,5,7,9,10,12,14,19,21,35,r|
[LogP]

-1.591 (est)
[CAS DataBase Reference]

19210-12-9(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P301+P312+P330
[Hazard Codes ]

Xn
[Risk Statements ]

R22:Harmful if swallowed.
[Safety Statements ]

S22:Do not breathe dust .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

3172
[WGK Germany ]

3
[HS Code ]

29389090
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Hazard InformationBack Directory
[Chemical Properties]

White crystalline powder, easily soluble in methanol and water, derived from Scrophularia ningpoensis and Uncaria rhynchophylla.
[Uses]

Harpagoside is an iridoid glycoside along with with Harpagide (H105270), the potential to be strong anti-inflammatory agents providing the bulk of the observed effects from their plant origins.
[Definition]

ChEBI: Harpagoside is a terpene glycoside.
[Biological Activity]

Harpagoside is an orally available iridoid glycoside and an active component of Harpagophytum extract with cardioprotective effects. Harpagoside is shown to directly bind to and activate ACE2. Allosterically inhibits ACE2 binding to spike protein and reduces viral entry and lessen SARS-CoV-2 infection. Harpagoside was reported to suppress AP-1IL-6COX-1/2c-FOSNF-ĸB expression and upregulate BMP2 and Wnt signaling pathways.
[in vivo]

Harpagoside (5 mg/kg; 15 mg/kg; po; once daily for 60 days) has potential neuroprotective effects against Aβ intoxication in an Aβ1-40-induced rat Alzheimer's disease (AD) model[3].

[IC 50]

COX-1; COX-2
Spectrum DetailBack Directory
[Spectrum Detail]

Harpagoside(19210-12-9)MS
Harpagoside(19210-12-9)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

19210-12-9(sigmaaldrich)
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