CAS 479-98-1|Aucubin

Introduction：Basic information about CAS 479-98-1|Aucubin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Aucubin BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles129
6. Synonyms

Common Name	Aucubin
CAS Number	479-98-1	Molecular Weight	346.330
Density	1.6±0.1 g/cm3	Boiling Point	669.0±55.0 °C at 760 mmHg
Molecular Formula	C₁₅H₂₂O₉	Melting Point	180 - 184ºC
MSDS	ChineseUSA	Flash Point	358.4±31.5 °C

Names

Name	Aucubin
Synonym	More Synonyms

Aucubin BiologicalActivity

Description	Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities.IC50 value:Target:In vitro: Aucubin promotes neuronal differentiation and neurite outgrowth in neural stem cells cultured primarily from the rat embryonic hippocampus [1]. Aucubin significantly reversed the elevated gene and protein expression of MMP-3, MMP-9, MMP-13, iNOS, COX-2 and the production of NO induced by IL-1β challenge in rat chondrocytes [2]. In vivo:
Related Catalog	Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/ImmunologyNatural Products >>Terpenoids and Glycosides
References	[1]. Sheng-nan Wang, et al. Aucubin prevents interleukin-1 beta induced inflammation and cartilage matrix degradation via inhibition of NF-κB signaling pathway in rat articular chondrocytes. International Immunopharmacology, Volume 24, Issue 2, February 2015 [2]. Xue B, et al. Pharmacokinetics and tissue distribution of Aucubin, Ajugol and Catalpol in rats using a validated simultaneous LC-ESI-MS/MS assay. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:245-53. [3]. Shirley KP, et al. In Vitro Effects of Plantago Major Extract, Aucubin, and Baicalein on Candida Albicans Biofilm Formation, Metabolic Activity, and Cell Surface Hydrophobicity. J Prosthodont. 2015 Nov 30. [4]. Yong Min Kim, et al. Aucubin Promotes Neurite Outgrowth in Neural Stem Cells and Axonal Regeneration in Sciatic Nerves. Exp Neurobiol. 2014 Sep; 23(3): 238–245.

Description

Aucubin is an iridoid glycoside with a wide range of biological activities, including anti-inflammatory, anti-microbial, anti-algesic as well as anti-tumor activities.IC50 value:Target:In vitro: Aucubin promotes neuronal differentiation and neurite outgrowth in neural stem cells cultured primarily from the rat embryonic hippocampus [1]. Aucubin significantly reversed the elevated gene and protein expression of MMP-3, MMP-9, MMP-13, iNOS, COX-2 and the production of NO induced by IL-1β challenge in rat chondrocytes [2]. In vivo:

Related Catalog

Signaling Pathways >>Others >>OthersResearch Areas >>Inflammation/ImmunologyNatural Products >>Terpenoids and Glycosides

References

[1]. Sheng-nan Wang, et al. Aucubin prevents interleukin-1 beta induced inflammation and cartilage matrix degradation via inhibition of NF-κB signaling pathway in rat articular chondrocytes. International Immunopharmacology, Volume 24, Issue 2, February 2015

[2]. Xue B, et al. Pharmacokinetics and tissue distribution of Aucubin, Ajugol and Catalpol in rats using a validated simultaneous LC-ESI-MS/MS assay. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:245-53.

[3]. Shirley KP, et al. In Vitro Effects of Plantago Major Extract, Aucubin, and Baicalein on Candida Albicans Biofilm Formation, Metabolic Activity, and Cell Surface Hydrophobicity. J Prosthodont. 2015 Nov 30.

[4]. Yong Min Kim, et al. Aucubin Promotes Neurite Outgrowth in Neural Stem Cells and Axonal Regeneration in Sciatic Nerves. Exp Neurobiol. 2014 Sep; 23(3): 238–245.

Chemical & Physical Properties

Density	1.6±0.1 g/cm3
Boiling Point	669.0±55.0 °C at 760 mmHg
Melting Point	180 - 184ºC
Molecular Formula	C₁₅H₂₂O₉
Molecular Weight	346.330
Flash Point	358.4±31.5 °C
Exact Mass	346.126373
PSA	149.07000
LogP	-3.17
Vapour Pressure	0.0±4.6 mmHg at 25°C
Index of Refraction	1.660
InChIKey	RJWJHRPNHPHBRN-FKVJWERZSA-N
SMILES	OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O)C3O)C12
Storage condition	2-8°C

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	Xn
Risk Phrases	R22
Safety Phrases	S22-S45
RIDADR	NONH for all modes of transport
WGK Germany	3

Articles129

Binding properties of antimicrobial agents to lipid membranes using surface plasmon resonance.

Biol. Pharm. Bull. 37(8) , 1383-9, (2014)

In the present study, we examined the interaction of antimicrobial agents with four model lipid membranes that mimicked mammalian cell membranes and Gram-positive and -negative bacterial membranes and...

Positive cooperativity between acceptor and donor sites of the peptidoglycan glycosyltransferase.

Biochem. Pharmacol. 93(2) , 141-50, (2015)

The glycosyltransferases of family 51 (GT51) catalyze the polymerization of lipid II to form linear glycan chains, which, after cross linking by the transpeptidases, form the net-like peptidoglycan ma...

Investigation of the interactions between the EphB2 receptor and SNEW peptide variants.

Growth Factors 32(6) , 236-46, (2014)

EphB2 interacts with cell surface-bound ephrin ligands to relay bidirectional signals. Overexpression of the EphB2 receptor protein has been linked to different types of cancer. The SNEW (SNEWIQPRLPQH...

Synonyms

Rhimanthin

EINECS 207-540-8

Aucubin

Rhinanthin

(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)tetrahydro-2H-pyran-3,4,5-triol

Rhimantin

(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl β-D-glucopyranoside

β-D-Glucopyranoside, (1S,4aR,5S,7aS)-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl

AUCUBOSIDE

[1S-(1a,4aa,5a,7a)]-1,4a,5,7a-Tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-b-D-glucopyranoside

MFCD00136026

(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxyméthyl)-1,4a,5,7a-tétrahydrocyclopenta[c]pyran-1-yl]oxy}-6-(hydroxyméthyl)tétrahydro-2H-pyran-3,4,5-triol

(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyr-1-yl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyr-1-yl-β-D-glucopyranoside

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