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MedKoo Cat#: 146281 | Name: Simmondsin

Description:

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

Simmondsin is a naturally occurring compound found in jojoba (Simmondsia chinensis) seeds, known for its appetite-suppressing properties. It has been studied for potential use in weight management and obesity treatment due to its ability to reduce food intake in animals. Simmondsin is believed to act by influencing satiety signals, possibly through modulation of cholecystokinin (CCK), a hormone involved in appetite regulation.

Chemical Structure

Simmondsin
Simmondsin
CAS#51771-52-9

Theoretical Analysis

MedKoo Cat#: 146281

Name: Simmondsin

CAS#: 51771-52-9

Chemical Formula: C16H25NO9

Exact Mass: 375.1529

Molecular Weight: 375.37

Elemental Analysis: C, 51.20; H, 6.71; N, 3.73; O, 38.36

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
Simmondsin;
IUPAC/Chemical Name
(Z)-2-((2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)cyclohexylidene)acetonitrile
InChi Key
KURSRHBVYUACKS-XGYNEUJOSA-N
InChi Code
1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3+/t8-,9+,10-,11+,12-,13+,14-,15+,16-/m1/s1
SMILES Code
CO[C@H]1C[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)\C(=C/C#N)[C@H](O)[C@H]1OC
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 375.37 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: Boozer CN, Herron AJ. Simmondsin for weight loss in rats. Int J Obes (Lond). 2006 Jul;30(7):1143-8. doi: 10.1038/sj.ijo.0803251. Epub 2006 Feb 7. PMID: 16462820. 2: Lievens S, Flo G, Decuypere E, Van Boven M, Cokelaere M. Simmondsin: effects on meal patterns and choice behavior in rats. Physiol Behav. 2003 Apr;78(4-5):669-77. doi: 10.1016/s0031-9384(03)00039-8. PMID: 12782222. 3: Cokelaere MM, Busselen P, Flo G, Daenens P, Decuypere E, Kühn E, Van Boven M. Devazepide reverses the anorexic effect of simmondsin in the rat. J Endocrinol. 1995 Dec;147(3):473-7. doi: 10.1677/joe.0.1470473. PMID: 8543917. 4: Van Boven M, Laga M, Leonard S, Busson R, Holser R, Decuypere E, Flo G, Lievens S, Cokelaere M. Mechanism of simmondsin decomposition during sodium hydroxide treatment. J Agric Food Chem. 2003 Feb 26;51(5):1260-4. doi: 10.1021/jf025812o. PMID: 12590465. 5: Lievens S, Verbaeys I, Flo G, Briers R, Decuypere E, Cokelaere M. Disruption of the behavioral satiety sequence by simmondsin. Appetite. 2009 Jun;52(3):703-710. doi: 10.1016/j.appet.2009.03.010. Epub 2009 Mar 28. PMID: 19501769. 6: Feki F, Mahmoudi A, Denev P, Feki I, Ognyanov M, Georgiev Y, Choura S, Chamkha M, Trendafilova A, Sayadi S. A jojoba (Simmondsia chinensis) seed cake extracts express hepatoprotective activity against paracetamol-induced toxicity in rats. Biomed Pharmacother. 2022 Sep;153:113371. doi: 10.1016/j.biopha.2022.113371. Epub 2022 Jul 4. PMID: 35797942. 7: Flo G, Vermaut S, Darras VM, Van Boven M, Decuypere E, Kühn ER, Daenens P, Cokelaere M. Effects of simmondsin on food intake, growth, and metabolic variables in lean (+/?) and obese (fa/fa) Zucker rats. Br J Nutr. 1999 Feb;81(2):159-67. PMID: 10450335. 8: Cokelaere M, Daenens P, Decuypere E, Flo G, Kühn E, Van Boven M, Vermaut S. Reproductive performance of rats treated with defatted jojoba meal or simmondsin before or during gestation. Food Chem Toxicol. 1998 Jan;36(1):13-9. doi: 10.1016/s0278-6915(97)00118-x. PMID: 9487360. 9: Flo G, Van Boven M, Vermaut S, Daenens P, Decuypere E, Cokelaere M. The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat. Appetite. 2000 Apr;34(2):147-51. doi: 10.1006/appe.1999.0299. PMID: 10744903. 10: Cokelaere M, Daenens P, Van Boven M, Kühn ER, Decuypere E, Darras V. Influence of long-term simmondsin administration on thyroid hormone levels in adult rats. Horm Metab Res. 1995 Jul;27(7):318-21. doi: 10.1055/s-2007-979969. PMID: 7590614. 11: Baek JS, Kim HY, Abbott TP, Moon TW, Lee SB, Park CS, Park KH. Acarviosine- simmondsin, a novel compound obtained from acarviosine-glucose and simmondsin by Thermus maltogenic amylase and its in vivo effect on food intake and hyperglycemia. Biosci Biotechnol Biochem. 2003 Mar;67(3):532-9. doi: 10.1271/bbb.67.532. PMID: 12723600. 12: Van Boven M, Daenens P, Cokelaere M, Decuypere E. Extraction and liquid chromatographic method for the determination of simmondsin in plasma. J Chromatogr B Biomed Appl. 1994 May 13;655(2):281-5. doi: 10.1016/0378-4347(94)00121-9. PMID: 8081475. 13: Van Boven M, Holser R, Cokelaere M, Flo G, Decuypere E. Gas chromatographic analysis of simmondsins and simmondsin ferulates in jojoba meal. J Agric Food Chem. 2000 Sep;48(9):4083-6. doi: 10.1021/jf0004107. PMID: 10995318. 14: Flo G, Vermaut S, Van Boven M, Daenens P, Buyse J, Decuypere E, Kühn E, Cokelaere M. Comparison of the effects of simmondsin and cholecystokinin on metabolism, brown adipose tissue and the pancreas in food-restricted rats. Horm Metab Res. 1998 Aug;30(8):504-8. doi: 10.1055/s-2007-978921. PMID: 9761380. 15: Belhadj S, Hentati O, Hamdaoui G, Fakhreddine K, Maillard E, Dal S, Sigrist S. Beneficial Effect of Jojoba Seed Extracts on Hyperglycemia-Induced Oxidative Stress in RINm5f Beta Cells. Nutrients. 2018 Mar 20;10(3):384. doi: 10.3390/nu10030384. PMID: 29558444; PMCID: PMC5872802. 16: Tietel Z, Melamed S, Eretz-Kdosha N, Guetta A, Gvirtz R, Ogen-Shtern N, Dag A, Cohen G. Anti-Herpes Simplex 1 Activity of Simmondsia chinensis (Jojoba) Wax. Molecules. 2021 Oct 7;26(19):6059. doi: 10.3390/molecules26196059. PMID: 34641603; PMCID: PMC8512747. 17: Alonso-Castro AJ, Domínguez F, Zapata-Morales JR, Carranza-Álvarez C. Plants used in the traditional medicine of Mesoamerica (Mexico and Central America) and the Caribbean for the treatment of obesity. J Ethnopharmacol. 2015 Dec 4;175:335-45. doi: 10.1016/j.jep.2015.09.029. Epub 2015 Sep 26. PMID: 26410815. 18: Feki F, Klisurova D, Masmoudi MA, Choura S, Denev P, Trendafilova A, Chamkha M, Sayadi S. Optimization of microwave assisted extraction of simmondsins and polyphenols from Jojoba (Simmondsia chinensis) seed cake using Box-Behnken statistical design. Food Chem. 2021 Sep 15;356:129670. doi: 10.1016/j.foodchem.2021.129670. Epub 2021 Mar 23. PMID: 33812189. 19: Van Boven M, Leyssen T, Busson R, Holser R, Cokelaere M, Flo G, Decuypere E. Identification of 4,5-didemethyl-4-O-alpha-D-glucopyranosylsimmondsin and pinitol alpha-D-galactosides in jojoba seed meal (Simmondsia chinensis). J Agric Food Chem. 2001 Sep;49(9):4278-83. doi: 10.1021/jf010380n. PMID: 11559123. 20: Lein S, Van Boven M, Holser R, Decuypere E, Flo G, Lievens S, Cokelaere M. Simultaneous determination of carbohydrates and simmondsins in jojoba seed meal (Simmondsia chinensis) by gas chromatography. J Chromatogr A. 2002 Nov 22;977(2):257-64. doi: 10.1016/s0021-9673(02)01410-3. PMID: 12456116.