IUPAC/Chemical Name
Cyclopenta(c)pyran-1,5-diol, 1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, (1R-(1alpha,4aalpha,5alpha,7aalpha))-
InChi Key
BACWCXKATFIVFS-JQCXWYLXSA-N
InChi Code
InChI=1S/C9H12O4/c10-4-5-3-7(11)6-1-2-13-9(12)8(5)6/h1-3,6-12H,4H2/t6-,7+,8+,9+/m0/s1
SMILES Code
O[C@H]1[C@@]2([H])[C@@]([C@H](O)C=C2CO)([H])C=CO1
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
>3 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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
184.19
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.
| 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: Lv PY, Feng H, Huang WH, Tian YY, Wang YQ, Qin YH, Li XH, Hu K, Zhou HH, Ouyang DS. Aucubin and its hydrolytic derivative attenuate activation of hepatic stellate cells via modulation of TGF-β stimulation. Environ Toxicol Pharmacol. 2017 Mar;50:234-239. doi: 10.1016/j.etap.2017.02.012. Epub 2017 Feb 8. PubMed PMID: 28199906.
2: Li Y, Zhao Y, Zhang YM, Wang MJ, Sun WJ. X-ray crystal structure of iridoid glucoside aucubin and its aglycone. Carbohydr Res. 2009 Nov 2;344(16):2270-3. doi: 10.1016/j.carres.2009.08.021. Epub 2009 Aug 24. PubMed PMID: 19762008.
3: Kang Z, Wu WH, Wang JJ, Ouyang DS. [Research advances in pharmacology of aucubin and aucubigenin]. Zhongguo Zhong Yao Za Zhi. 2007 Dec;32(24):2585-7. Review. Chinese. PubMed PMID: 18338591.
4: Lee DH, Cho IG, Park MS, Kim KN, Chang IM, Mar W. Studies on the possible mechanisms of protective activity against alpha-amanitin poisoning by aucubin. Arch Pharm Res. 2001 Feb;24(1):55-63. PubMed PMID: 11235813.
5: Kim DH, Kim BR, Kim JY, Jeong YC. Mechanism of covalent adduct formation of aucubin to proteins. Toxicol Lett. 2000 Apr 3;114(1-3):181-8. PubMed PMID: 10713483.
6: Bartholomaeus A, Ahokas J. Inhibition of P-450 by aucubin: is the biological activity of aucubin due to its glutaraldehyde-like aglycone? Toxicol Lett. 1995 Oct;80(1-3):75-83. PubMed PMID: 7482595.
7: Ishiguro K, Yamaki M, Takagi S. [Studies on the iridoid related compounds. I. On the antimicrobial activity of aucubigenin and certain iridoid aglycones]. Yakugaku Zasshi. 1982 Aug;102(8):755-9. Japanese. PubMed PMID: 7175693.
