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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 400106321
| Watchedfields = changed
⚫ | verifiedrevid = 470470833
| ImageFile = Sterubin.png | ImageFile = Sterubin.png
| ImageSize = 200px | ImageSize = 200px
| IUPACName = 2-(3,4-Dihydroxy-phenyl)-5-hydroxy-7-methoxy-chroman-4-one | IUPACName = (2''S'')-3′,4′,5-Trihydroxy-7-methoxyflavan-4-one
| SystematicName = (2''S'')-2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-2,3-dihydro-4''H''-1-benzopyran-4-one
| OtherNames = 7-Methoxy-3',4',5-trihydroxyflavanone | OtherNames = 7-Methoxy-3′,4′,5-trihydroxyflavanone
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1064932 | ChemSpiderID = 1064932
Line 14: Line 17:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DSAJORLEPQBKDA-AWEZNQCLSA-N | StdInChIKey = DSAJORLEPQBKDA-AWEZNQCLSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 51857-11-5 | CASNo = 51857-11-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0IT00NY6AC
| PubChem = 1268276 | PubChem = 1268276
| SMILES = O=C2c3c(O(c1ccc(O)c(O)c1)C2)cc(OC)cc3O | SMILES = O=C2c3c(O(c1ccc(O)c(O)c1)C2)cc(OC)cc3O
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>16</sub>H<sub>14</sub>O<sub>6</sub> | Formula = C<sub>16</sub>H<sub>14</sub>O<sub>6</sub>
| MolarMass = 302.28 g/mol | MolarMass = 302.28 g/mol
| Appearance = | Appearance =
| Density = | Density = 1.458 g/mL
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}


'''Sterubin''' (7-methoxy-3',4',5-trihydroxyflavanone) is a ] flavanone extracted from Herba Santa ('']'') a plant growing in ].<ref>Patricia Kaminski and Richard Katz. . Flower Essence Society.</ref> '''Sterubin''' (7-methoxy-3',4',5-trihydroxyflavanone) is a ] flavanone extracted from Yerba Santa ('']'') a plant growing in ].<ref>Patricia Kaminski and Richard Katz. . Flower Essence Society.</ref>


Sterubin is one of the four ]s identified by ] in this plant which elicit taste-modifying properties. The others are ], its sodium salt, and ].<ref>{{cite journal |author=Ley JP, Krammer G, Reinders G, Gatfield IL, Bertram HJ |title=Evaluation of bitter masking flavanones from Herba Santa (''Eriodictyon californicum'' (H. and A.) Torr., Hydrophyllaceae) |journal=J. Agric. Food Chem. |volume=53 |issue=15 |pages=6061–6 |year=2005 |month=July |pmid=16028996 |doi=10.1021/jf0505170 }}</ref> Sterubin is one of the four ]s identified by ] in this plant which elicit taste-modifying properties. The others are ], its sodium salt, and ].<ref>{{cite journal |vauthors=Ley JP, Krammer G, Reinders G, Gatfield IL, Bertram HJ |title=Evaluation of bitter masking flavanones from Herba Santa (''Eriodictyon californicum'' (H. and A.) Torr., Hydrophyllaceae) |journal=J. Agric. Food Chem. |volume=53 |issue=15 |pages=6061–6 |date=July 2005 |pmid=16028996 |doi=10.1021/jf0505170 }}</ref>


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.<ref>{{cite journal |author1=Wolfgang Fischer |author2=Antonio Currais |author3=Zhibin Liang |author4=Antonio Pinto |author5=Pamela Maher |title=Old age-associated phenotypic screening for Alzheimer's disease drug candidates identifies sterubin as a potent neuroprotective compound from Yerba santa |journal=Redox Biology |volume=21 |date=February 2019 |page=101089 |pmid=30594901 |doi=10.1016/j.redox.2018.101089 |pmc=6309122 }}</ref><ref>{{cite journal |author1=Zhibin Liang |author2=Pamela Maher |title=Structural Requirements for the Neuroprotective and Anti-Inflammatory Activities of the Flavanone Sterubin |journal=Antioxidants |volume=11 |date=November 2022 |issue=11 |page=2197 |pmid=36358569 |pmc=9686938 |doi=10.3390/antiox11112197 |doi-access=free }}</ref><ref>Batya Swift Yasgur. . (Paywalled) Medscape. February 2019.</ref>
⚫ ==References==

⚫ == References ==
{{Reflist}} {{Reflist}}


{{Flavanone}} {{Flavanone}}


] ]
] ]
] ]
] ]
]


⚫ {{ketone-stub}}


⚫ {{aromatic-stub}}
]

Latest revision as of 00:30, 3 December 2023

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
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: DSAJORLEPQBKDA-AWEZNQCLBS
SMILES
  • O=C2c3c(O(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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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.

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.

References

  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. . (Paywalled) Medscape. February 2019.
Flavanones and their glycosides
Flavanones
O-methylated flavanones
C-methylated flavanones
Glycosides
Acetylated
Acetylated glycosides


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