Synonym
Talaumidin; (-)-Talaumidin; (2S,3S,4S,5S)-Talaumidin;
IUPAC/Chemical Name
4-((2S,3S,4S,5S)-5-(benzo[d][1,3]dioxol-5-yl)-3,4-dimethyltetrahydrofuran-2-yl)-2-methoxyphenol
InChi Key
JPDORDSJPIKURD-HIGYNYDNSA-N
InChi Code
InChI=1S/C20H22O5/c1-11-12(2)20(14-5-7-16-18(9-14)24-10-23-16)25-19(11)13-4-6-15(21)17(8-13)22-3/h4-9,11-12,19-21H,10H2,1-3H3/t11-,12-,19-,20-/m0/s1
SMILES Code
COC1=C(O)C=CC([C@H]2O[C@H](C3=CC4=C(OCO4)C=C3)[C@@H](C)[C@@H]2C)=C1
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
342.39
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: Koriyama Y, Furukawa A, Sugitani K, Kubo M, Harada K, Fukuyama Y. Talaumidin Promotes Neurite Outgrowth of Staurosporine-Differentiated RGC-5 Cells Through PI3K/Akt-Dependent Pathways. Adv Exp Med Biol. 2018;1074:649-653. doi: 10.1007/978-3-319-75402-4_79. PubMed PMID: 29721999.
2: Harada K, Zaha K, Bando R, Irimaziri R, Kubo M, Koriyama Y, Fukuyama Y. Structure-activity relationships of talaumidin derivatives: Their neurite-outgrowth promotion in vitro and optic nerve regeneration in vivo. Eur J Med Chem. 2018 Mar 25;148:86-94. doi: 10.1016/j.ejmech.2018.02.014. Epub 2018 Feb 9. PubMed PMID: 29454919.
3: Harada K, Kubo M, Horiuchi H, Ishii A, Esumi T, Hioki H, Fukuyama Y. Systematic Asymmetric Synthesis of All Diastereomers of (-)-Talaumidin and Their Neurotrophic Activity. J Org Chem. 2015 Jul 17;80(14):7076-88. doi: 10.1021/acs.joc.5b00945. Epub 2015 Jul 6. PubMed PMID: 26108800.
4: Xue P, Wang LP, Jiao XZ, Jiang YJ, Xiao Q, Luo ZG, Xie P, Liang XT. Total synthesis of (-)-talaumidin and (-)-galbelgin. J Asian Nat Prod Res. 2009;11(3):281-7. doi: 10.1080/10286020802675191. PubMed PMID: 19408154.
5: Kim H, Wooten CM, Park Y, Hong J. Stereoselective synthesis of tetrahydrofuran lignans via BF(3) x OEt(2)-promoted reductive deoxygenation/epimerization of cyclic hemiketal: synthesis of (-)-odoratisol C, (-)-futokadsurin A, (-)-veraguensin, (+)-fragransin A(2), (+)-galbelgin, and (+)-talaumidin. Org Lett. 2007 Sep 27;9(20):3965-8. Epub 2007 Sep 1. PubMed PMID: 17764190.
6: Zhai H, Nakatsukasa M, Mitsumoto Y, Fukuyama Y. Neurotrophic effects of talaumidin, a neolignan from Aristolochia arcuata, in primary cultured rat cortical neurons. Planta Med. 2004 Jul;70(7):598-602. PubMed PMID: 15303251.
