Simmondsin

Simmondsin
Clinical data
ATC code	none;
Identifiers
	IUPAC name (2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2R,3R,4S,5S,6R)-3,4,;
CAS Number	51771-52-9;
PubChem CID	6437384;
ChemSpider	4941947;
UNII	O51H15R39K;
CompTox Dashboard (EPA)	DTXSID901027519 ;
Chemical and physical data
Formula	C16H25NO9
Molar mass	375.374 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N#C\C=C2/[C@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)C[C@H](OC)[C@H](OC)[C@H]2O;
	InChI InChI=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; Key:KURSRHBVYUACKS-XGYNEUJOSA-N;
	(verify)

Simmondsin is a component of jojoba seeds (pronounced "ho-HO-bah") (Simmondsia chinensis). While it had been considered toxic due to jojoba seed meal causing weight loss in animals, in recent years its appetite suppressant effect has also been researched as a potential treatment for obesity.^[1] It is thought to reduce appetite by increasing levels of cholecystokinin.^[2]^[3]^[4]^[5]

References

^ "Simmondsin From Jojoba - Checked for Appetite Suppression". United States Department of Agriculture, Agricultural Research Service.
^ Cokelaere MM, Busselen P, Flo G, Daenens P, Decuypere E, Kühn E, Van Boven M (December 1995). "Devazepide reverses the anorexic effect of simmondsin in the rat". The Journal of Endocrinology. 147 (3): 473–7. doi:10.1677/joe.0.1470473. PMID 8543917.
^ Flo G, Vermaut S, Van Boven M, Daenens P, Buyse J, Decuypere E, et al. (August 1998). "Comparison of the effects of simmondsin and cholecystokinin on metabolism, brown adipose tissue and the pancreas in food-restricted rats". Hormone and Metabolic Research. 30 (8): 504–8. doi:10.1055/s-2007-978921. PMID 9761380. S2CID 260166054.
^ Flo G, Van Boven M, Vermaut S, Daenens P, Decuypere E, Cokelaere M (April 2000). "The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat". Appetite. 34 (2): 147–51. doi:10.1006/appe.1999.0299. PMID 10744903. S2CID 42949049.
^ Boozer CN, Herron AJ (July 2006). "Simmondsin for weight loss in rats". International Journal of Obesity. 30 (7): 1143–8. doi:10.1038/sj.ijo.0803251. PMID 16462820. S2CID 1282460.

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[1] "Simmondsin From Jojoba - Checked for Appetite Suppression". United States Department of Agriculture, Agricultural Research Service.

[2] Cokelaere MM, Busselen P, Flo G, Daenens P, Decuypere E, Kühn E, Van Boven M (December 1995). "Devazepide reverses the anorexic effect of simmondsin in the rat". The Journal of Endocrinology. 147 (3): 473–7. doi:10.1677/joe.0.1470473. PMID 8543917.

[3] Flo G, Vermaut S, Van Boven M, Daenens P, Buyse J, Decuypere E, et al. (August 1998). "Comparison of the effects of simmondsin and cholecystokinin on metabolism, brown adipose tissue and the pancreas in food-restricted rats". Hormone and Metabolic Research. 30 (8): 504–8. doi:10.1055/s-2007-978921. PMID 9761380. S2CID 260166054.

[4] Flo G, Van Boven M, Vermaut S, Daenens P, Decuypere E, Cokelaere M (April 2000). "The vagus nerve is involved in the anorexigenic effect of simmondsin in the rat". Appetite. 34 (2): 147–51. doi:10.1006/appe.1999.0299. PMID 10744903. S2CID 42949049.

[5] Boozer CN, Herron AJ (July 2006). "Simmondsin for weight loss in rats". International Journal of Obesity. 30 (7): 1143–8. doi:10.1038/sj.ijo.0803251. PMID 16462820. S2CID 1282460.

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Clinical data

ATC code	none
Identifiers
IUPAC name (2Z)-2-[(2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-[(2R,3R,4S,5S,6R)-3,4,
CAS Number	51771-52-9
PubChem CID	6437384
ChemSpider	4941947
UNII	O51H15R39K
CompTox Dashboard (EPA)	DTXSID901027519
Chemical and physical data
Formula	C₁₆H₂₅NO₉
Molar mass	375.374 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES N#C\C=C2/[C@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)C[C@H](OC)[C@H](OC)[C@H]2O
InChI InChI=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 Key:KURSRHBVYUACKS-XGYNEUJOSA-N
(verify)