Sterubin

Sterubin
Names
	IUPAC name (2S)-3′,4′,5-Trihydroxy-7-methoxyflavan-4-one
	Systematic IUPAC name (2S)-2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one
	Other names 7-Methoxy-3′,4′,5-trihydroxyflavanone
Identifiers
CAS Number	51857-11-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	1064932 ;
PubChem CID	1268276;
UNII	0IT00NY6AC ;
CompTox Dashboard (EPA)	DTXSID70199819 ;
	InChI InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 Key: DSAJORLEPQBKDA-AWEZNQCLSA-N ; InChI=1/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 Key: DSAJORLEPQBKDA-AWEZNQCLBS;
	SMILES O=C2c3c(O[C@H](c1ccc(O)c(O)c1)C2)cc(OC)cc3O;
Properties
Chemical formula	C16H14O6
Molar mass	302.28 g/mol
Density	1.458 g/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Sterubin (7-methoxy-3',4',5-trihydroxyflavanone) is a bitter-masking flavanone extracted from Yerba Santa (Eriodictyon californicum) a plant growing in America.^[1]

Sterubin is one of the four flavanones identified by Symrise in this plant which elicit taste-modifying properties. The others are homoeriodictyol, its sodium salt, and eriodictyol.^[2]

Recent research has demonstrated some neuroprotective properties of Sterubin in vitro, but more research is needed before it can be considered a true drug candidate.^[3]^[4]^[5]

References

^ Patricia Kaminski and Richard Katz. Yerba Santa Eriodictyon californicum. Flower Essence Society.
^ Ley JP, Krammer G, Reinders G, Gatfield IL, Bertram HJ (July 2005). "Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae)". J. Agric. Food Chem. 53 (15): 6061–6. doi:10.1021/jf0505170. PMID 16028996.
^ Wolfgang Fischer; Antonio Currais; Zhibin Liang; Antonio Pinto; Pamela Maher (February 2019). "Old age-associated phenotypic screening for Alzheimer's disease drug candidates identifies sterubin as a potent neuroprotective compound from Yerba santa". Redox Biology. 21: 101089. doi:10.1016/j.redox.2018.101089. PMC 6309122. PMID 30594901.
^ Zhibin Liang; Pamela Maher (November 2022). "Structural Requirements for the Neuroprotective and Anti-Inflammatory Activities of the Flavanone Sterubin". Antioxidants. 11 (11): 2197. doi:10.3390/antiox11112197. PMC 9686938. PMID 36358569.
^ Batya Swift Yasgur. [1]. (Paywalled) Medscape. February 2019.

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[1] Patricia Kaminski and Richard Katz. Yerba Santa Eriodictyon californicum. Flower Essence Society.

[2] Ley JP, Krammer G, Reinders G, Gatfield IL, Bertram HJ (July 2005). "Evaluation of bitter masking flavanones from Herba Santa (Eriodictyon californicum (H. and A.) Torr., Hydrophyllaceae)". J. Agric. Food Chem. 53 (15): 6061–6. doi:10.1021/jf0505170. PMID 16028996.

[3] Wolfgang Fischer; Antonio Currais; Zhibin Liang; Antonio Pinto; Pamela Maher (February 2019). "Old age-associated phenotypic screening for Alzheimer's disease drug candidates identifies sterubin as a potent neuroprotective compound from Yerba santa". Redox Biology. 21: 101089. doi:10.1016/j.redox.2018.101089. PMC 6309122. PMID 30594901.

[4] Zhibin Liang; Pamela Maher (November 2022). "Structural Requirements for the Neuroprotective and Anti-Inflammatory Activities of the Flavanone Sterubin". Antioxidants. 11 (11): 2197. doi:10.3390/antiox11112197. PMC 9686938. PMID 36358569.

[5] Batya Swift Yasgur. [1]. (Paywalled) Medscape. February 2019.

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v t e Flavanones and their glycosides
Flavanones	Butin Eriodictyol Naringenin Pinocembrin
O-methylated flavanones	Alpinetin Hesperetin Homoeriodictyol Isosakuranetin Pinostrobin (Pinocembrin-7-methylether) Sakuranetin Sterubin
C-methylated flavanones	Poriol
Glycosides	Eriocitrin Neoeriocitrin Hesperidin Liquiritin Naringin (Narigenin 7-O-neohesperidoside) Narirutin (Naringenin 7-O-rutinoside) Poncirin Prunin (Naringenin-7-O-glucoside) Sakuranin
Acetylated	8-Prenylnaringenin Isoxanthohumol Sophoraflavanone G
Acetylated glycosides	Nirurin

Names

IUPAC name (2S)-3′,4′,5-Trihydroxy-7-methoxyflavan-4-one
Systematic IUPAC name (2S)-2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names 7-Methoxy-3′,4′,5-trihydroxyflavanone
Identifiers
CAS Number	51857-11-5^Y
3D model (JSmol)	Interactive image
ChemSpider	1064932^Y
PubChem CID	1268276
UNII	0IT00NY6AC^Y
CompTox Dashboard (EPA)	DTXSID70199819
InChI InChI=1S/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1^Y Key: DSAJORLEPQBKDA-AWEZNQCLSA-N^Y InChI=1/C16H14O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1 Key: DSAJORLEPQBKDA-AWEZNQCLBS
SMILES O=C2c3c(O[C@H](c1ccc(O)c(O)c1)C2)cc(OC)cc3O
Properties
Chemical formula	C₁₆H₁₄O₆
Molar mass	302.28 g/mol
Density	1.458 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references