Yamataimine

CAS# 67113-69-3

Yamataimine

Catalog No. BCN2064----Order now to get a substantial discount!

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Quality Control of Yamataimine

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Chemical structure

Yamataimine

3D structure

Chemical Properties of Yamataimine

Cas No. 67113-69-3 SDF Download SDF
PubChem ID 181871 Appearance Powder
Formula C18H27NO5 M.Wt 337.41
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CCC1CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)C
Standard InChIKey RRIMIQDGHHBXCP-BXPDPKNNSA-N
Standard InChI InChI=1S/C18H27NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h5,11-12,14-15,22H,4,6-10H2,1-3H3/t11-,12+,14-,15-,18+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Protocol of Yamataimine

Structure Identification
Rapid Commun Mass Spectrom. 2008;22(4):591-602.

Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang).[Pubmed: 18220326]


METHODS AND RESULTS:
Senecio scandens Buch.-Ham is a plant source for a commonly used traditional Chinese medicinal (TCM) herb Qianliguang. A TCM herbal proprietary product containing Qianliguang as the major herb for the treatment of sinusitis has been used in China for several decades, and has also been exported to other regions and countries worldwide. In the present study, the aqueous extract of S. scandens collected in the Shanxi Province of China was determined, for the first time, to contain hepatotoxic and tumorigenic pyrrolizidine alkaloids (PAs) by using high-performance liquid chromatography/mass spectrometric (HPLC/MS) analysis in various scanning modes. A total of nine toxic and two non-toxic PAs were detected in the aqueous extract of S. scandens, of which six PAs, namely neoplatyphylline, senecionine, senecionine N-oxide, seneciphylline, seneciphylline N-oxide and senkirkine, were unequivocally characterized, while other PAs were tentatively assigned as jacobine, jacozine N-oxide (or erucifoline N-oxide), 7-tigloylplatynecine, usaramine and an isomer of Yamataimine. The estimated total content of toxic PAs in S. scandens was 10.82 microg/g herb, which was significantly higher than that (> or =1 microg/g herb) recommended by Belgium and Germany not to be used clinically.
CONCLUSIONS:
Among the PAs definitively identified, senecionine, seneciphylline, and senkirkine are known tumorigens capable of inducing liver tumors in experimental animals, while seneciphylline N-oxide and senecionine N-oxide are probably tumorigenic due to their potential conversion into seneciphylline and senecionine via metabolic reduction in the body. Thus, the current finding of the presence of toxic/tumorigenic PAs in S. scandens challenges the safety of using this TCM herb and its proprietary products.

Bulletin of the Chemical Society of Japan (Impact Factor: 2.22). 11/1994; 67(11):3094-3099.

Enantioselective Synthesis of the Macrocyclic Pyrrolizidine Alkaloid Yamataimine[Reference: WebLink]


METHODS AND RESULTS:
Described is a short-step synthesis of optically active Yamataimine, a 12-membered pyrrolizidine alkaloid of retronecine type. Methyl (1S,SR)-5-methyl-2-oxocyclopentanecarboxylate derived from (R)-(+)-pulegone was converted into the necic acid component required for the synthesis of Yamataimine, in a nine-step sequence. Regioselective coupling of (+)-retronecine with the necic acid component via tin-mediated regioselective acylation followed by macrolactonization led to the first synthesis of (+)-Yamataimine.
CONCLUSIONS:
Enantioselective Synthesis of the Macrocyclic Pyrrolizidine Alkaloid Yamataimine.

Yamataimine Dilution Calculator

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Yamataimine Molarity Calculator

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Preparing Stock Solutions of Yamataimine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9638 mL 14.8188 mL 29.6375 mL 59.2751 mL 74.0938 mL
5 mM 0.5928 mL 2.9638 mL 5.9275 mL 11.855 mL 14.8188 mL
10 mM 0.2964 mL 1.4819 mL 2.9638 mL 5.9275 mL 7.4094 mL
50 mM 0.0593 mL 0.2964 mL 0.5928 mL 1.1855 mL 1.4819 mL
100 mM 0.0296 mL 0.1482 mL 0.2964 mL 0.5928 mL 0.7409 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Yamataimine

Identification of five hepatotoxic pyrrolizidine alkaloids in a commonly used traditional Chinese medicinal herb, Herba Senecionis scandentis (Qianliguang).[Pubmed:18220326]

Rapid Commun Mass Spectrom. 2008;22(4):591-602.

Senecio scandens Buch.-Ham is a plant source for a commonly used traditional Chinese medicinal (TCM) herb Qianliguang. A TCM herbal proprietary product containing Qianliguang as the major herb for the treatment of sinusitis has been used in China for several decades, and has also been exported to other regions and countries worldwide. In the present study, the aqueous extract of S. scandens collected in the Shanxi Province of China was determined, for the first time, to contain hepatotoxic and tumorigenic pyrrolizidine alkaloids (PAs) by using high-performance liquid chromatography/mass spectrometric (HPLC/MS) analysis in various scanning modes. A total of nine toxic and two non-toxic PAs were detected in the aqueous extract of S. scandens, of which six PAs, namely neoplatyphylline, senecionine, senecionine N-oxide, seneciphylline, seneciphylline N-oxide and senkirkine, were unequivocally characterized, while other PAs were tentatively assigned as jacobine, jacozine N-oxide (or erucifoline N-oxide), 7-tigloylplatynecine, usaramine and an isomer of Yamataimine. The estimated total content of toxic PAs in S. scandens was 10.82 microg/g herb, which was significantly higher than that (> or =1 microg/g herb) recommended by Belgium and Germany not to be used clinically. Among the PAs definitively identified, senecionine, seneciphylline, and senkirkine are known tumorigens capable of inducing liver tumors in experimental animals, while seneciphylline N-oxide and senecionine N-oxide are probably tumorigenic due to their potential conversion into seneciphylline and senecionine via metabolic reduction in the body. Thus, the current finding of the presence of toxic/tumorigenic PAs in S. scandens challenges the safety of using this TCM herb and its proprietary products.

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