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{{chembox
{{chembox
| Watchedfields = changed
| verifiedrevid = 440125457
| verifiedrevid = 440125457
| Name = Engeletin
| Name = Engeletin
| ImageFile = Engeletin.PNG
| ImageFile = Engeletin.svg
| ImageSize = 200px
| ImageSize = 200px
| ImageName = Chemical structure of engeletin
| ImageName = Chemical structure of engeletin
| ImageAlt = Chemical structure of engeletin
| ImageAlt = Chemical structure of engeletin
| IUPACName = (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
| IUPACName = (2''R'',3''R'')-4′,5,7-Trihydroxy-3-(α-<small>L</small>-rhamnopyranosyloxy)flavan-4-one
| PIN = (2''R'',3''R'')-5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-{[(2''S'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4''H''-1-benzopyran-4-one
| OtherNames = [[dihydrokaempferol]] 3-[[rhamnoside]]<br>Engelitin
| OtherNames = [[dihydrokaempferol]] 3-[[rhamnoside]]<br>Engelitin
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 572-31-6
| CASNo = 572-31-6
| CASNo_Ref = {{cascite|correct|??}}=
| CASNo_Ref = {{cascite|correct|??}}=
| CASOther =
| CASNoOther =
| PubChem = 6453452
| PubChem = 6453452
| SMILES = CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
| SMILES = CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
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| MeSHName =
| MeSHName =
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>21</sub>H<sub>22</sub>O<sub>10</sub>
| C=21 | H=22 | O=10
| MolarMass = 434.39 g/mol
| ExactMass = 434.121297 u
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt = <!-- °C -->
| MeltingPt =
| BoilingPt = <!-- °C -->
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| AutoignitionPt =
| Autoignition =
| RPhrases = <!-- {{R10}}, {{R23}}, {{R34}}, {{R50}} etc. -->
| GHS_ref = <!-- no GHS data found in PubChem Dec2021 -->
| SPhrases = <!-- {{S1/2}}, {{S9}}, {{S16}}, {{S26}}, {{S36/37/39}}, {{S45}}, {{S61}} etc. -->
}}
}}
}}
}}
'''Engeletin''' is a phenolic compound found in [[wine]]<ref>Astilbin engeletin in grapes and wine. Eugene K. Trousdale and Vernon L. Singleton, Phytochemistry, Volume 22, Issue 2, 1983, Pages 619-620, {{doi|10.1016/0031-9422(83)83072-6}}</ref> and isolated from the bark of ''[[Hymenaea martiana]]''.<ref>Isolation, Chemical Identification and Pharmacological Evaluation of Eucryphin, Astilbin and Engelitin Obtained from the Bark of Hymenaea martiana. Eliane Carneiro, João B. Calixto, Franco Delle Monache‌and Rosendo A. Yunes, Pharmaceutical Biology, 1993, Vol. 31, No. 1, Pages 38-46, {{doi|10.3109/13880209309082916}}</ref>
'''Engeletin''' is a [[flavanonol]] [[rhamnoside]], a phenolic compound found in [[wine]]<ref>{{ cite journal |author1=Trousdale, E. K. |author2=Singleton, V. L. | title = Astilbin and Engeletin in Grapes and Wine | journal = Phytochemistry | year = 1983 | volume = 22 | issue = 2 | pages = 619–20 | doi = 10.1016/0031-9422(83)83072-6 }}</ref> and isolated from the bark of ''[[Hymenaea martiana]]''.<ref>{{ cite journal |author1=Carneiro, E. |author2=Calixto, J. B. |author3=Monache‌, F. D. |author4=Yunes, R. A. | title = Isolation, Chemical Identification and Pharmacological Evaluation of Eucryphin, Astilbin and Engelitin Obtained from the Bark of ''Hymenaea martiana'' | journal = Pharmaceutical Biology | year = 1993 | volume = 31 | issue = 1 | pages = 38–46 | doi = 10.3109/13880209309082916 }}</ref>


== See also ==
== See also ==
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[[Category:Flavonoid rhamnosides]]
[[Category:Flavonoid rhamnosides]]
[[Category:Phenolic compounds in wine]]
[[Category:Phenolic compounds found in Fabaceae]]



{{Natural-phenol-stub}}
{{aromatic-stub}}

Latest revision as of 01:23, 1 May 2023

Engeletin
Chemical structure of engeletin
Names
IUPAC name
(2R,3R)-4′,5,7-Trihydroxy-3-(α-L-rhamnopyranosyloxy)flavan-4-one
Preferred IUPAC name
(2R,3R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names
Identifiers
3D model (JSmol)
  • CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
Properties
C21H22O10
Molar mass 434.397 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Engeletin is a flavanonol rhamnoside, a phenolic compound found in wine[1] and isolated from the bark of Hymenaea martiana.[2]

See also

[edit]

References

[edit]
  1. ^ Trousdale, E. K.; Singleton, V. L. (1983). "Astilbin and Engeletin in Grapes and Wine". Phytochemistry. 22 (2): 619–20. doi:10.1016/0031-9422(83)83072-6.
  2. ^ Carneiro, E.; Calixto, J. B.; Monache‌, F. D.; Yunes, R. A. (1993). "Isolation, Chemical Identification and Pharmacological Evaluation of Eucryphin, Astilbin and Engelitin Obtained from the Bark of Hymenaea martiana". Pharmaceutical Biology. 31 (1): 38–46. doi:10.3109/13880209309082916.


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