ChemicalBook CAS DataBase List 479-98-1

479-98-1

Name	Aucubin
CAS	479-98-1
EINECS(EC#)	207-540-8
Molecular Formula	C15H22O9
MDL Number	MFCD00136026
Molecular Weight	346.33
MOL File	479-98-1.mol

Synonyms

AUCUBIN AUCUBOSIDE B-D-GLUCOPYRANOSIDE, (1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(HYDROXYMETHYL)CYCLOPENTA[C]PYRAN-1-YL RHINANTHIN 1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside [1S-(1alpha,4aalpha,5alpha,7aalpha)]-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside AUCUBINB-D-GLUCOPYRANOSIDE, (1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(HYDROXYMETHYL)CYCLOPENTA[C]PYRAN-1-YL, Aucubin std. AUCUBIN(P) AUCUBIN hplc (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol AUCUBIN WITH HPLC [c]pyran-1-yl tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta β-D-Glucopyranoside, (1S,4aR,5S,7aS)-1,4a,5,7a- b-D-Glucopyranoside, 1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl, [1S-(1a,4a,5a,7a)] Rhimantin 1S-(1alpha,4aalpha,5alpha,7aalpha)-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside [(1S)-1,4aα,5,7aα-Tetrahydro-5α-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1α-yl]β-D-glucopyranoside Aucubigenin 1-O-β-D-glucopyranoside

Chemical Properties

Melting point	181°
alpha	D21 -163.1° (c = 1.6)
Boiling point	669.0±55.0 °C(Predicted)
density	1.61±0.1 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMF: 30 mg/ml; DMSO: 30 mg/ml; PBS (pH 7.2): 10 mg/ml
form	neat
pka	12.80±0.70(Predicted)
color	White
Optical Rotation	-16518 (H2O)
BRN	50340
Major Application	food and beverages
InChI	InChI=1/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/s3
InChIKey	RJWJHRPNHPHBRN-FKVJWERZSA-N
SMILES	[C@@]12([H])C(CO)=C[C@@H](O)[C@]1([H])C=CO[C@H]2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O \|&1:0,6,8,13,15,16,18,19,21,r\|
LogP	-4.103 (est)
CAS DataBase Reference	479-98-1(CAS DataBase Reference)

Safety Data

Risk Statements	R22:Harmful if swallowed. less more
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) . less more
WGK Germany	3
F	10-23
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral

Hazard Information

Chemical Properties

Aucubin, bitter in taste, easily soluble in water, ethanol, methanol, insoluble in chloroform, ether, petroleum ether and other solvents. It is a kind of iridoid compound that widely exists in many plant species in nature.

Uses

Aucubine 5-Acetatea is an impurity of Aucubine (A794730). Aucubine shows antioxidant and protective effects for the liver and kidney organs, shown in mice with induced diabetes.

Definition

ChEBI: Aucubin is an organic molecular entity. It has a role as a metabolite.

Mechanism of action

Aucubin can be used to clear dampness and heat, facilitate urination, relieving pain, reduce blood pressure and protecting liver. It can promote the regeneration of stem cells, significantly inhibit the replication of hepatitis B virus DNA.

in vivo

Aucubin (5 mg/kg; i.p. for 15 d) has antioxidant and pancreas-protective effects on rats with streptozotocin-induced diabetes^[1].
Aucubin (40-200 mg/kg; a single i.p.) exhibits significant protective activity against α-amanitin intoxication in mice^[5].
Aucubin (5 mg/kg/day; i.p. for 21 d) decreases the breathing frequency, increases the lung dynamic compliance, alleviates lung parenchymal fibrotic changes, and reduces the intrapulmonary collagen disposition and inflammatory injury of BLM-stimulated mice^[6].

Animal Model:	Male Wistar rats (200-230 g) induced diabetes by a injection of streptozotocin^[1]
Dosage:	5 mg/kg
Administration:	I.p. twice daily for the first 5 days, followed by single injections daily for the last 10 days
Result:	Increased the body weight of streptozotocin-diabetic rats. Lowered the blood glucose level. Decreased the level of lipid peroxidation and increased the activities of antioxidant enzymes. Increased in insulin immunoreactivity and the number of immunoreactive β cells compared with untreated diabetic rats.

storage

Store at -20°C

Material Safety Data Sheet(MSDS)

Spectrum Detail

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