ChemicalBook--->CAS DataBase List--->28608-75-5

28608-75-5

28608-75-5 Structure

28608-75-5 Structure
IdentificationBack Directory
[Name]

ORIENTIN
[CAS]

28608-75-5
[Synonyms]

lutexin
ORIENTIN
ORIENTINE
Polygonin
Aids026706
Aids-026706
ORIENTIN(P)
ORIENTIN(SH)
ORIDONIN (RG)
Orientin,Lutexin
orientin(flavone)
8-Glucosylluteolin
ORIENTIN WITH HPLC
ORIENTIN USP/EP/BP
luteolin8-glucoside
LUTEOLIN-8-C-GLUCOSIDE
Luteolin 8-C-β-D-glucopyranoside
Orientin, froM PolygonuM orientale
Luteolin 8-C-beta-D-Glucopyranoside
Orientin, 98%, from Polygonum orientale
Orientin, 98%, from Polygonum orientale L.
8-β-D-Glucopyranosyl-3',4',5,7-tetrahydroxyflavone
8-beta-D-Glucopyranosyl-3',4',5,7-tetrahydroxyflavone
2-(3,4-dihydroxyphenyl)-8-beta-d-glucopyranosyl-5,7-dihydroxy-4h-1-benzopyra
4h-1-benzopyran-4-one,2-(3,4-dihydroxyphenyl)-8-beta-d-glucopyranosyl-5,7-dihy
2-(3,4-Dihydroxyphenyl)-8-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-β-D-glucopyranosyl-5,7-dihydroxy-
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-8-(β-D-glucopyranosyl)-4H-1-benzopyran-4-one
2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-.beta.-D-glucopyranosyl-5,7-dihydroxy-
[Molecular Formula]

C21H20O11
[MDL Number]

MFCD00017432
[MOL File]

28608-75-5.mol
[Molecular Weight]

448.38
Chemical PropertiesBack Directory
[Melting point ]

260-285°C
[Boiling point ]

816.1±65.0 °C(Predicted)
[density ]

1.759±0.06 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Sealed in dry,2-8°C
[solubility ]

1 M NaOH: soluble1mg/mL, clear, yellow-orange
[form ]

powder
[pka]

6.24±0.40(Predicted)
[color ]

yellow
[Stability:]

Hygroscopic
[Major Application]

metabolomics
vitamins, nutraceuticals, and natural products
[InChIKey]

PLAPMLGJVGLZOV-FYNBPVOANA-N
[SMILES]

C12OC(=CC(=O)C=1C(=CC(O)=C2[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)O)C1C=CC(O)=C(O)C=1 |&1:12,13,15,16,18,r|
[LogP]

1.580 (est)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P280-P301+P312-P302+P352-P305+P351+P338
[Safety Statements ]

24/25
[WGK Germany ]

3
[RTECS ]

DJ3009300
[HS Code ]

29389090
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

Orientin is a flavone glycoside originally isolated from P. orientale that has diverse biological activities, including antioxidant, antibacterial, and anti-inflammatory properties. Orientin scavenges 2,2-diphenyl-1-picryl-hydrazyl (DPPH; Item No. 14805) radicals with an IC50 value of 316.21 μg/ml. It also decreases the cytopathic effects of parainfluenza type 3 virus with an IC50 value of 11.7 μg/ml and a cytotoxic concentration (CC50) value of 375 μg/ml in Hep-2 cells. Orientin (5-40 μM) inhibits LPS-induced barrier disruption, decreases the expression of toll-like receptor 4 (TLR4), phosphorylated p38, and NF-κB, and decreases TNF-α production and IL-6 secretion in a dose-dependent manner in human umbilical vein endothelial cells (HUVECs). It also prolongs survival in a mouse model of LPS-induced lethal endotoxemia when administered at a dose of 36 μg/animal 12 hours after LPS administration.
[Chemical Properties]

Yellow powder
[Uses]

Orientin is a flavone, a chemical flavonoid compound. Orientin have been investigated for its anti-oxidant, antihypertensive and antihyperlipidemic effects.
[Definition]

ChEBI: A C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8.
[in vivo]

Orientin (0.1–10 mg/kg for p.o.;once) inhibits allergic reaction in PCA mouse model[1].
Orientin (10–40 mg/kg for i.p.;once daily for 12 days) has an anti-neuroinflammatory effect in SNL rat model[2].

Animal Model:PCA mouse model[1]
Dosage:0.1–10 mg/kg
Administration:Oral gavage (p.o.); Euthanized mouse after 1 h
Result:Significantly suppressed PCA reactions in PCA mouse model.
Animal Model:SNL rat model[2]
Dosage:10, 20, 40 mg/kg
Administration:Intraperitoneal injection (i.p.); Once daily for 12 days
Result:Alleviated the downreg-ulation of PWL and promoted the behavior recovery in SNL rat model.
Decreased the levels of IL-6, IL-1β and TNF-α.
Increased the level of anti-inflammatory IL-10.
Down-regulated the level of MDA.
[References]

[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] NAN WU. Antioxidant activities of extracts and main components of Pigeonpea [Cajanus cajan (L.) Millsp.] leaves.[J]. Molecules, 2009, 14 3: 1032-1043. DOI: 10.3390/molecules14031032
[3] YAO-LAN LI . Antiviral activities of flavonoids and organic acid from Trollius chinensis Bunge[J]. Journal of ethnopharmacology, 2002, 79 3: Pages 365-368. DOI: 10.1016/s0378-8741(01)00410-x
[4] WONHWA LEE  Jong S B  Sae Kwang Ku. Vascular barrier protective effects of orientin and isoorientin in LPS-induced inflammation in vitro and in vivo[J]. Vascular pharmacology, 2014, 62 1: Pages 3-14. DOI: 10.1016/j.vph.2014.04.006
Spectrum DetailBack Directory
[Spectrum Detail]

ORIENTIN(28608-75-5)1HNMR
ORIENTIN(28608-75-5)IR1
ORIENTIN(28608-75-5)IR2
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