Synonym
Turneforcidine; Racemonecine;
IUPAC/Chemical Name
(1R,7R,7aR)-7-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol
InChi Key
QWOXSTGOGUNUGF-XLPZGREQSA-N
InChi Code
1S/C8H15NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h6-8,10-11H,1-5H2/t6-,7+,8+/m0/s1
SMILES Code
[H][C@@]12[C@H](O)CCN1CC[C@H]2CO
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
157.21
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: Liang YF, Chung CC, Huang MW, Uang BJ. Formal syntheses of (-)-isoretronecanol, (+)-laburnine, and a concise enantioselective synthesis of (+)-turneforcidine. J Antibiot (Tokyo). 2019 Jun;72(6):397-406. doi: 10.1038/s41429-019-0169-9. Epub 2019 Mar 20. PMID: 30894676.
2: Wee AG. A dirhodium(II)-carbenoid route to (-)- and (+)-Geissman-Waiss lactone: synthesis of (1R,7R,8R)-(-)-turneforcidine. J Org Chem. 2001 Dec 14;66(25):8513-7. doi: 10.1021/jo010753j. PMID: 11735532.
3: Vanecko JA, West FG. Ring expansion of azetidinium ylides: rapid access to the pyrrolizidine alkaloids turneforcidine and platynecine. Org Lett. 2005 Jul 7;7(14):2949-52. doi: 10.1021/ol050915o. PMID: 15987177.
4: An DK, Duncan D, Livinghouse T, Reid P. A concise synthesis of turneforcidine via a metalloiminium ion cyclization terminated by the 2-(methylthio)-3-(trimethylsilyl)-1-propenyl moiety. Org Lett. 2001 Sep 20;3(19):2961-3. doi: 10.1021/ol010122b. PMID: 11554818.
5: Hendriks H, Balraadjsing W, Huizing HJ, Bruins AP. Investigation into the Presence of Pyrrolizidine Alkaloids in Eupatorium cannabinum by Means of Positive and Negative Ion Chemical Ionization GC-MS. Planta Med. 1987 Oct;53(5):456-61. doi: 10.1055/s-2006-962772. PMID: 17269067.
6: Hartmann T, Theuring C, Beuerle T, Bernays EA, Singer MS. Acquisition, transformation and maintenance of plant pyrrolizidine alkaloids by the polyphagous arctiid Grammia geneura. Insect Biochem Mol Biol. 2005 Oct;35(10):1083-99. doi: 10.1016/j.ibmb.2005.05.011. PMID: 16102415.
7: Marín Loaiza JC, Ernst L, Beuerle T, Theuring C, Céspedes CL, Hartmann T. Pyrrolizidine alkaloids of the endemic Mexican genus Pittocaulon and assignment of stereoisomeric 1,2-saturated necine bases. Phytochemistry. 2008 Jan;69(1):154-67. doi: 10.1016/j.phytochem.2007.07.004. Epub 2007 Aug 23. PMID: 17719067.
