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MedKoo Cat#: 600114 | Name: Aucubin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.

Chemical Structure

Aucubin
Aucubin
CAS#479-98-1

Theoretical Analysis

MedKoo Cat#: 600114

Name: Aucubin

CAS#: 479-98-1

Chemical Formula: C15H22O9

Exact Mass: 346.1264

Molecular Weight: 346.33

Elemental Analysis: C, 52.02; H, 6.40; O, 41.58

Price and Availability

Size Price Availability Quantity
5mg USD 160.00
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Related CAS #
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Synonym
IUPAC/Chemical Name
[1S-(1alpha,4aalpha,5alpha,7aalpha)]-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside
InChi Key
RJWJHRPNHPHBRN-ACALXYEMSA-N
InChi Code
InChI=1S/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+/m0/s1
SMILES Code
O[C@H]([C@H]([C@@H]([C@H](CO)O1)O)O)[C@H]1O[C@H]2[C@]3([H])C(C(O)C=C3CO)C=CO2
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 346.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Zhang L, Ma YL, Liu Y, Zu YG. Development and validation of high liquid performance chromatography-tandem mass spectrometry method for simultaneous determination of geniposidic acid and aucubin in rat plasma for pharmacokinetic study after oral administration of Du-zhong tea extract. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Jul 15;963:62-9. doi: 10.1016/j.jchromb.2014.04.033. Epub 2014 May 23. PubMed PMID: 24929551. 2: Lee GH, Lee MR, Lee HY, Kim SH, Kim HK, Kim HR, Chae HJ. Eucommia ulmoides cortex, geniposide and aucubin regulate lipotoxicity through the inhibition of lysosomal BAX. PLoS One. 2014 Feb 19;9(2):e88017. doi: 10.1371/journal.pone.0088017. eCollection 2014. PubMed PMID: 24586300; PubMed Central PMCID: PMC3929538. 3: Lee HY, Lee GH, Lee MR, Kim HK, Kim NY, Kim SH, Lee YC, Kim HR, Chae HJ. Eucommia ulmoides Oliver extract, aucubin, and geniposide enhance lysosomal activity to regulate ER stress and hepatic lipid accumulation. PLoS One. 2013 Dec 11;8(12):e81349. doi: 10.1371/journal.pone.0081349. eCollection 2013. PubMed PMID: 24349058; PubMed Central PMCID: PMC3859480. 4: Park KS. Aucubin, a naturally occurring iridoid glycoside inhibits TNF-α-induced inflammatory responses through suppression of NF-κB activation in 3T3-L1 adipocytes. Cytokine. 2013 Jun;62(3):407-12. doi: 10.1016/j.cyto.2013.04.005. Epub 2013 Apr 20. PubMed PMID: 23612013. 5: Lemus C, Poleschak M, Gailly S, Desage-El Murr M, Koch M, Deguin B. Lewis acid catalyzed enlargement of cyclic β-alkoxyenals and one-pot synthesis of polyfunctional enoxysilanes derived from aucubin with trimethylsilyldiazomethane. Chemistry. 2013 Apr 8;19(15):4686-90. doi: 10.1002/chem.201203968. Epub 2013 Feb 28. PubMed PMID: 23450668. 6: Zheng J, Liu D, Zhao SQ, Su J, Yan QP, Chen L, Xiao Y, Zhang CM. [Enzymatic extraction and antibacterial activity of aucubin from Eucommia ulmoides leaves]. Zhong Yao Cai. 2012 Feb;35(2):304-6. Chinese. PubMed PMID: 22822679. 7: Xue HY, Lu YN, Fang XM, Xu YP, Gao GZ, Jin LJ. Neuroprotective properties of aucubin in diabetic rats and diabetic encephalopathy rats. Mol Biol Rep. 2012 Oct;39(10):9311-8. doi: 10.1007/s11033-012-1730-9. Epub 2012 Jul 19. PubMed PMID: 22810648. 8: Xu W, Deng Z, Guo H, Ling P. A rapid and sensitive determination of aucubin in rat plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetic application. Biomed Chromatogr. 2012 Sep;26(9):1066-70. doi: 10.1002/bmc.1748. Epub 2011 Nov 23. PubMed PMID: 22113886. 9: Hajimehdipoor H, Shekarchi M, Piralihamedani M, Abedi Z, Zahedi H, Shekarchi M, Gohari AR. A Validated HPTLC-Densitometric Method for Assay of Aucubin in Vitexagnus-castusL. Iran J Pharm Res. 2011 Fall;10(4):705-10. PubMed PMID: 24250405; PubMed Central PMCID: PMC3813080.