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Revision as of 19:01, 12 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit		Latest revision as of 00:48, 17 December 2024 edit undoArthurfragoso (talk | contribs)Extended confirmed users2,076 edits Fixes image on dark mode
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	{{Refimprove|date=June 2008}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 400526680
			| Watchedfields = changed
⚫	|Reference=<ref>'']'', 11th Edition, '''6367'''.</ref>
		⚫	| verifiedrevid = 428801080
⚫	|ImageFile=Neohesperidin_dihydrochalcone.png
		⚫	| Reference=<ref>'']'', 11th Edition, '''6367'''.</ref>
⚫	|ImageSize=200px
		⚫	| ImageFile=Neohesperidin_dihydrochalcone.png
	|IUPACName= 1-oxy]-2-tetrahydropyranyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-methoxyphenyl)propan-1-one</small>
		⚫	| ImageSize=200px
⚫	|OtherNames=
			| ImageClass=skin-invert
			| IUPACName=1-{2,6-Dihydroxy-4-phenyl}-3-(3-hydroxy-4-methoxyphenyl)propan-1-one
			| SystematicName=(1<sup>2</sup>''S'',1<sup>3</sup>''R'',1<sup>4</sup>''R'',1<sup>5</sup>''R'',1<sup>6</sup>''S'',3<sup>2</sup>''S'',3<sup>3</sup>''R'',3<sup>4</sup>''S'',3<sup>5</sup>''S'',3<sup>6</sup>''R'')-1<sup>3</sup>,1<sup>4</sup>,1<sup>5</sup>,3<sup>4</sup>,3<sup>5</sup>,5<sup>3</sup>,5<sup>5</sup>,9<sup>3</sup>-Octahydroxy-3<sup>6</sup>-(hydroxymethyl)-9<sup>4</sup>-methoxy-1<sup>6</sup>-methyl-2,4-dioxa-1(2),3(3,2)-bis(oxana)-5(1,4),9(1)-dibenzenanonaphan-6-one
		⚫	| OtherNames=
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo=20702-77-6		| CASNo=20702-77-6
⚫	| PubChem=30231
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| SMILES=C1((((O1)O2(((O2OC3=CC(=C(C(=C3)O)C(=O)CCC4=CC(=C(C=C4)OC) O)O)CO)O)O)O)O)O
			| UNII = 3X476D83QV
		⚫	| PubChem=30231
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 83535
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 28072
			| InChI = 1/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
			| InChIKey = ITVGXXMINPYUHD-CUVHLRMHBZ
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C28H36O15/c1-11-21(34)23(36)25(38)27(40-11)43-26-24(37)22(35)19(10-29)42-28(26)41-13-8-16(32)20(17(33)9-13)14(30)5-3-12-4-6-18(39-2)15(31)7-12/h4,6-9,11,19,21-29,31-38H,3,5,10H2,1-2H3/t11-,19+,21-,22+,23+,24-,25+,26+,27-,28+/m0/s1
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = ITVGXXMINPYUHD-CUVHLRMHSA-N
		⚫	| SMILES=C1((((O1)O2(((O2OC3=CC(=C(C(=C3)O)C(=O)CCC4=CC(=C(C=C4)OC)O)O)CO)O)O)O)O)O
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>28</sub>H<sub>36</sub>O<sub>15</sub>		| Formula = C<sub>28</sub>H<sub>36</sub>O<sub>15</sub>
	| MolarMass = 612.58 g/mol		| MolarMass = 612.58 g/mol
			| Appearance=
	| ExactMass = 582.194856
	| Appearance=		| Density=
	| Density=		| MeltingPt=
	| MeltingPt=		| BoilingPt=
	| BoilingPt=		| Solubility=
	| Solubility=
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
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	'''Neohesperidin dihydrochalcone''', sometimes abbreviated to '''neohesperidin DC''' or simply '''NHDC''', is an ] derived from ].		'''Neohesperidin dihydrochalcone''', sometimes abbreviated to '''neohesperidin DC''' or simply '''NHDC''', is an ] derived from ].
		⚫	It is particularly effective in masking the bitter tastes of other compounds found in citrus, including ] and ]. Industrially, it is produced by extracting neohesperidin from the ], and then hydrogenating this to make NHDC.
⚫	NHDC was discovered during the 1960s as part of a ] research program to find methods for minimizing the taste of bitter flavorants in citrus juices. ] is one such bitter compound. When treated with ] or another strong base, and then ] ], it becomes NHDC, a compound roughly 1500-1800 times sweeter than sugar at threshold concentrations; around 340 times sweeter than sugar weight-for-weight. Its potency is naturally affected by such factors as the application in which it is used, and the ] of the product.
			==Discovery==
⚫	Like other highly sweet ]s, such as ] and those found in ], NHDC's sweet taste has a slower onset than sugar's and lingers in the mouth for some time. Unlike ], NHDC is stable to elevated temperatures and to acidic or basic conditions, and so can be used in applications that require a long shelf life. NHDC itself can stay foodsafe for up to five years when stored in optimal conditions.
		⚫	NHDC was discovered during the 1960s as part of a ] research program to find methods for minimizing the taste of bitter flavorants in citrus juices. ] is one such bitter compound. When treated with ] or another strong base, and then ] ], it becomes NHDC.
	The ] approved NHDC's use as a sweetener in 1994. It has not been approved as a sweetener in the ]. It is sometimes said that NHDC is considered a ] flavour enhancer by the Flavour and Extract Manufacturers' Association, which is a trade group with no legal standing. NHDC has never appeared on the FDA's GRAS listing.
			== Profile ==
⚫	It is particularly effective in masking the bitter tastes of other compounds found in citrus, including ] and ]. Industrially, it is produced by extracting neohesperidin from the ], and then hydrogenating this to make NHDC.
			NHDC in pure form is found as a white substance not unlike ]. It has an intense sweet taste because it stimulates the sweet receptor ]+] in humans,<ref name="Winnig">{{Cite journal|last1=Winnig|first1=Marcel|last2=Bufe|first2=Bernd|last3=Kratochwil|first3=Nicole A.|last4=Slack|first4=Jay P.|last5=Meyerhof|first5=Wolfgang|date=2007-10-12|title=The binding site for neohesperidin dihydrochalcone at the human sweet taste receptor|journal=BMC Structural Biology|volume=7|issue=1|pages=66|doi=10.1186/1472-6807-7-66|issn=1472-6807|pmc=2099433|pmid=17935609 |doi-access=free }}</ref> although this is species-dependent, as the equivalent receptor in rats does not respond to the molecule.<ref name="Winnig" />
			It is roughly 1500–1800 times sweeter than sugar at threshold concentrations; around 340 times sweeter than sugar. Its potency is naturally affected by such factors as the application in which it is used, and the ] of the product.
			Like other highly sweet ]s, such as ] and those found in ], NHDC's sweet taste has a slower onset than sugar's and lingers in the mouth for some time.
		⚫	Unlike ], NHDC is stable to elevated temperatures and to acidic or basic conditions, and so can be used in applications that require a long shelf life. NHDC itself can stay foodsafe for up to five years when stored in optimal conditions.
	The product is well known for having a strong synergistic effect when used in conjunction with other ]s such as ], ], ], and ], as well as sugar alcohols such as ]. NHDC usage boosts the effects of these sweeteners at lower concentrations than would otherwise be required; smaller amounts of other sweeteners are needed. This provides a cost benefit.		The product is well known for having a strong synergistic effect when used in conjunction with other ]s such as ], ], ], and ], as well as sugar alcohols such as ]. NHDC usage boosts the effects of these sweeteners at lower concentrations than would otherwise be required; smaller amounts of other sweeteners are needed. This provides a cost benefit.
			== Approval and safety ==
	As a ], NHDC is used in a wide range of products and is indicated by the ] E 959. It is noted particularly for enhancing ] effects (known in the industry as 'mouth feel'). An example of this is 'creaminess' in ] foods such as ] and ], but is also widely favoured for use in otherwise naturally ] products. ] companies are fond of the product as a means of reducing the bitterness of ] ] in ] form, and it has been used for ] feed as a means of reducing feeding time. Other products NHDC can be found in may include a wide variety of ]s (and non-alcoholic), ] foods, ], ] and ]s such as ] and ].
			NHDC is approved in the ] as sweetener (E-959) since 1994, as well as flavouring (FL-16.061). It is also listed as a ] (GRAS) flavour enhancer by the ].<ref>{{Cite web|last1=Cohen|first1=S.M.|last2=Eisenbrand|first2=G|last3=Fukushima|first3=S|last4=Gooderham|first4=N.J.|last5=Guengerich|first5=F.P.|last6=Hecht|first6=S.S.|last7=Rietjens|first7=I.M.C.M.|last8=Harman|first8=C|last9=Taylor|first9=S.V.|display-authors=1|date=July 2018|title=GRAS 28 Flavoring Substances|url=https://www.femaflavor.org/sites/default/files/2018-07/gras28-cohen_et_al_2018.pdf|access-date=2018-08-08|website=FEMA}}</ref>
⚫	NHDC in pure form is found as a white substance not unlike ]. In food it is used as a ] in concentrations of around 4-5 ] (ppm) and as an ] at around 15-20 ppm.
			In November 2020,<ref>{{Cite web|title=GRAS Notices|url=https://www.cfsanappsexternal.fda.gov/scripts/fdcc/index.cfm?set=GRASNotices&id=902|access-date=2021-01-08|website=www.cfsanappsexternal.fda.gov|language=en-US}}</ref> the ] issued a no objection letter to the GRAS status of Neohesperidin dihydrochalcone (NHDC). The ] concluded that NHDC is GRAS (based on scientific procedures) for its intended use as a sweetener in various food categories at maximum levels of 10–1000 ppm.
	Research has shown that at strengths of around and above 20 ppm, NHDC can produce side effects such as ] and ]. This is not widely documented, however is unquestionably known within the ] communities that have worked with the product, and many recommend wearing a ] when handling pure NHDC.
			NHDC is also included both in ] and ], for being used as ] in drug products.
⚫	==References==
			The safety of NHDC has been extensively tested.<ref>'']'', 4th Edition, '''722'''.</ref> Safety studies have indicated that NHDC is neither toxic, mutagenic nor carcinogenic.<ref>'']'', J. Smith, 1st Edition, '''70'''.</ref> Like other flavonoids, NHDC is easily metabolized by intestinal microbiota to innocuous products.<ref>'']'', EFSA Journal 2010; 8(9):1065</ref>
			The safety of NHDC has been thoroughly tested again by the ] in 2022. The ] was set at 20&nbsp;mg/kg of body weight.<ref>{{Cite journal |last1=EFSA Panel on Food Additives and Flavourings (FAF) |last2=Younes |first2=Maged |last3=Aquilina |first3=Gabriele |last4=Castle |first4=Laurence |last5=Degen |first5=Gisela |last6=Engel |first6=Karl-Heinz |last7=Fowler |first7=Paul J |last8=Frutos Fernandez |first8=Maria José |last9=Fürst |first9=Peter |last10=Gundert-Remy |first10=Ursula |last11=Gürtler |first11=Rainer |last12=Husøy |first12=Trine |last13=Manco |first13=Melania |last14=Mennes |first14=Wim |last15=Moldeus |first15=Peter |date=November 2022 |title=Re-evaluation of neohesperidine dihydrochalcone (E 959) as a food additive |journal=EFSA Journal |volume=20 |issue=11 |pages=e07595 |doi=10.2903/j.efsa.2022.7595 |pmc=9669802 |pmid=36406883}}</ref>
			== Uses ==
		⚫	In food it is used as a ] in concentrations of around 4–5 ] (ppm) and as an ] at around 15–20 ppm.
			=== Masking ===
			] companies are fond of the product as a means of reducing the bitterness of ] ] in ] form, and it has been used for ] feed as a means of reducing feeding time. It is also widely favoured for use in otherwise naturally ] products.
			=== Enhancer ===
			As a ], NHDC is used in a wide range of products and is indicated by the ] E 959. It is noted particularly for enhancing ] effects (known in the industry as 'mouth feel'). An example of this is 'creaminess' in ] foods such as ] and ].
			=== Other uses ===
			Other products NHDC can be found in may include a wide variety of beverages,
			] and non-alcoholic, ] foods, ], ] and ]s such as ] and ]. NHDC is also used as ] in drug products to mask the bitter taste of some ].
		⚫	== References ==
	{{reflist}}		{{reflist}}
	==Internal link==		== Internal link ==
	* ]		* ]
	==External links==		==External links==
			*{{Commons category-inline}}
	* .		*.
	{{E number infobox 950-969}}		{{E number infobox 950-969}}
	{{Dihydrochalcone}}		{{Dihydrochalcone}}
	]		]
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]
	]