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{{chembox |
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{{chembox |
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| verifiedrevid = 400526611 |
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| verifiedrevid = 423307779 |
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|Reference= |
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| Reference = |
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|ImageFile=Naringin_dihydrochalcone.svg |
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| ImageFile =Naringin_dihydrochalcone.svg |
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|ImageSize=250px |
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| ImageSize =250px |
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|IUPACName= <small><nowiki>1-oxyoxan-2-yl]oxy-2, 6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one</nowiki> </small> |
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| IUPACName = 1-oxyoxan-2-yl]oxy-2, 6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one |
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| SystematicName = 3,5-Dihydroxy-4-phenyl 2-O-(6-deoxy-α-L-mannopyranosyl)-β-L-glucopyranoside |
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|OtherNames=Naringin DC |
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| OtherNames =Naringin DC |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=18916-17-1 |
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| CASNo =18916-17-1 |
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| PubChem=25245680 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=C1((((O1)O2(((OC2OC3=CC (=C(C(=C3)O)C(=O)CCC4=CC=C(C=C4)O)O)CO)O)O)O)O)O |
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| UNII = 7233QDO0QW |
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| PubChem =25245680 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 23089598 |
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| SMILES = C1((((O1)O2(((O2Oc3cc(c(c(c3)O)C(=O)CCc4ccc(cc4)O)O)CO)O)O)O)O)O |
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| InChI = 1/C27H34O14/c1-11-20(33)22(35)24(37)26(38-11)41-25-23(36)21(34)18(10-28)40-27(25)39-14-8-16(31)19(17(32)9-14)15(30)7-4-12-2-5-13(29)6-3-12/h2-3,5-6,8-9,11,18,20-29,31-37H,4,7,10H2,1H3/t11-,18-,20-,21-,22+,23+,24+,25-,26-,27-/m0/s1 |
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| InChIKey = CWBZAESOUBENAP-IKACCGSXBG |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C27H34O14/c1-11-20(33)22(35)24(37)26(38-11)41-25-23(36)21(34)18(10-28)40-27(25)39-14-8-16(31)19(17(32)9-14)15(30)7-4-12-2-5-13(29)6-3-12/h2-3,5-6,8-9,11,18,20-29,31-37H,4,7,10H2,1H3/t11-,18-,20-,21-,22+,23+,24+,25-,26-,27-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = CWBZAESOUBENAP-IKACCGSXSA-N |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=27 | H=34 | O=14 |
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| Formula = C<sub>27</sub>H<sub>34</sub>O<sub>14</sub> |
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| Appearance = White powder |
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| MolarMass= 582.55 g/mol |
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| Density = |
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| ExactMass = 582.194856 u |
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| Appearance = White powder |
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| MeltingPtC = 169 to 170 |
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| MeltingPt_notes = |
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| BoilingPt = |
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| MeltingPt = 169-170°C |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| MainHazards = |
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| FlashPt= |
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| FlashPt = |
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| AutoignitionPt = |
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| Autoignition= |
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'''Naringin dihydrochalcone''', sometimes abbreviated to '''naringin DC''', is an ] derived from ], a bitter compound found in ]<ref name=Ikan-1991> {{en}} Raphael Ikan. Natural products: a laboratory guide. Publié par Academic Press, 1991. 360 pages. ISBN 0123705517. Chapitre 1-Flavonoides, E. Synthesis of Naringin Dihydrochalcone— A Sweetening Agent. pages 17-18. </ref>. |
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'''Naringin dihydrochalcone''', sometimes abbreviated to '''naringin DC''', is an ] derived from ], a bitter compound found in ].<ref name=Ikan-1991>{{ Cite book | author = Ikan, R. | title = Natural Products: A Laboratory Guide | publisher = Academic Press | year = 1991 | edition = 2nd | isbn = 0-12-370551-7 | chapter = 1-Flavonoides. E. Synthesis of Naringin Dihydrochalcone — A Sweetening Agent | pages = 17–18 }}</ref> |
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Naringin ] is a ] ] discovered at the same time as ] during the 1960s as part of a ] research program to find methods for minimizing the taste of bitter flavorants in citrus juices. |
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Naringin ] is a ] ] discovered at the same time as ] during the 1960s as part of a ] research program to find methods for minimizing the taste of bitter flavorants in citrus juices. |
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When Naringin is treated with ] or another strong base, and then ] ], it becomes a dihydrochalcone, a compound roughly 300-1800 times sweeter than sugar at threshold concentrations<ref name=Tomasik-2003> {{en}} P Tomasik, Chemical and Functional Properties of Food Saccharides, CRC Press, 2003, 440 p. (ISBN 9780849314865), p. 389 </ref>. |
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When naringin is treated with ] or another strong base, and then ] ], it becomes a ] that is roughly 300–1800 times sweeter than sugar at threshold concentrations.<ref name=Tomasik-2003>{{ cite book | editor = Tomasik, P. | title = Chemical and Functional Properties of Food Saccharides | url = https://archive.org/details/chemicalfunction00toma_346 | url-access = limited | location = Boca Raton | publisher = CRC Press | year = 2003 | isbn = 978-0-84-931486-5 | page = }}</ref> |
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==References== |
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==References== |
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==External links== |
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*{{Commonscat-inline}} |
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{{Dihydrochalcone}} |
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{{Dihydrochalcone}} |
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{{Natural-phenol-stub}} |
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