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MedKoo Cat#: 146212 | Name: Thesinine

Description:

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

Thesinine is a pyrrolizidine alkaloid found in plants of the Boraginaceae family, such as Thesium species. It is part of a group of compounds known for their hepatotoxic and genotoxic potential due to their ability to form reactive metabolites. The mechanism of action involves metabolic activation in the liver to toxic pyrrole intermediates, which can bind to DNA and proteins, leading to cellular damage. While thesinine itself has limited therapeutic applications, it is significant in toxicological studies and in evaluating the safety of herbal medicines containing pyrrolizidine alkaloids.

Chemical Structure

Thesinine
Thesinine
CAS#488-02-8

Theoretical Analysis

MedKoo Cat#: 146212

Name: Thesinine

CAS#: 488-02-8

Chemical Formula: C17H21NO3

Exact Mass: 287.1521

Molecular Weight: 287.36

Elemental Analysis: C, 71.06; H, 7.37; N, 4.87; O, 16.70

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Thesinine;
IUPAC/Chemical Name
((1R,7aR)-hexahydro-1H-pyrrolizin-1-yl)methyl (E)-3-(4-hydroxyphenyl)acrylate
InChi Key
FQVNMXZPGWLUFZ-BNVCYRGBSA-N
InChi Code
1S/C17H21NO3/c19-15-6-3-13(4-7-15)5-8-17(20)21-12-14-9-11-18-10-1-2-16(14)18/h3-8,14,16,19H,1-2,9-12H2/b8-5+/t14-,16+/m0/s1
SMILES Code
OC1=CC=C(\C=C\C(=O)OC[C@@H]2CCN3CCC[C@H]23)C=C1
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 287.36 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: Koulman A, Seeliger C, Edwards PJ, Fraser K, Simpson W, Johnson L, Cao M, Rasmussen S, Lane GA. E/Z-Thesinine-O-4'-alpha-rhamnoside, pyrrolizidine conjugates produced by grasses (Poaceae). Phytochemistry. 2008 Jun;69(9):1927-32. doi: 10.1016/j.phytochem.2008.03.017. Epub 2008 May 6. PMID: 18466931. 2: Herrmann M, Joppe H, Schmaus G. Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis. Phytochemistry. 2002 Jun;60(4):399-402. doi: 10.1016/s0031-9422(02)00069-9. PMID: 12031432. 3: Wesseling AM, Demetrowitsch TJ, Schwarz K, Ober D. Variability of Pyrrolizidine Alkaloid Occurrence in Species of the Grass Subfamily Pooideae (Poaceae). Front Plant Sci. 2017 Nov 30;8:2046. doi: 10.3389/fpls.2017.02046. PMID: 29250094; PMCID: PMC5714882. 4: Gill GP, Bryant CJ, Fokin M, Huege J, Fraser K, Jones C, Cao M, Faville MJ. Low pyrrolizidine alkaloid levels in perennial ryegrass is associated with the absence of a homospermidine synthase gene. BMC Plant Biol. 2018 Apr 6;18(1):56. doi: 10.1186/s12870-018-1269-6. PMID: 29625552; PMCID: PMC5889531. 5: Jiang L, Zhang X, Chen X, He Y, Qiao L, Zhang Y, Li G, Xiang Y. Virtual Screening and Molecular Dynamics Study of Potential Negative Allosteric Modulators of mGluR1 from Chinese Herbs. Molecules. 2015 Jul 15;20(7):12769-86. doi: 10.3390/molecules200712769. PMID: 26184151; PMCID: PMC6332408. 6: Wang YH, Wang JH, He HP, Zhou H, Yang XW, Li CS, Hao XJ. Norsesquiterpenoid glucosides and a rhamnoside of pyrrolizidine alkaloid from Tephroseris kirilowii. J Asian Nat Prod Res. 2008 Jan-Feb;10(1-2):25-31. doi: 10.1080/10286020701273684. PMID: 18058377.