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Revision as of 12:37, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 418955872 of page Raspberry_ketone for the Chem/Drugbox validation project (updated: 'CASNo').		Latest revision as of 10:10, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,111 edits added Category:4-Hydroxyphenyl compounds using HotCat
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 414635343
			| Watchedfields = changed
	|Reference=<ref>''Catalog of Organics and Fine Chemicals'', Acros Organics, 2004/05, page 1250.</ref>
			| verifiedrevid = 464380314
	|ImageFile=Raspberry ketone.png
			| Reference = <ref>''Catalog of Organics and Fine Chemicals'', Acros Organics, 2004/05, page 1250.</ref>
	|ImageSize=200px
			| ImageFile = Raspberry Ketone Structure.png
	|IUPACName= 4-(4-Hydroxyphenyl) butan- 2-one
			| ImageSize = 200px
	|OtherNames=Frambinone<br>Oxyphenylon<br>Rheosmin<br>Rasketone
			| ImageAlt = Structural formula of raspberry ketone
	|Section1= {{Chembox Identifiers
			| ImageFile1 = Raspberry ketone 3D ball.png
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ImageAlt1 = Ball-and-stick model of raspberry ketone
			| PIN = 4-(4-Hydroxyphenyl)butan-2-one
			| OtherNames = ''p''-Hydroxybenzyl acetone; 4-(''p''-Hydroxyphenyl)-2-butanone; Frambinone; Oxyphenylon; Rheosmin; Rasketone
			|Section1={{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 20347		| ChemSpiderID = 20347
			| ChEBI_Ref = {{ebicite|correct|EBI}}
			| ChEBI = 68656
	| InChI = 1/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3		| InChI = 1/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3
	| InChIKey = NJGBTKGETPDVIK-UHFFFAOYAT		| InChIKey = NJGBTKGETPDVIK-UHFFFAOYAT
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = NJGBTKGETPDVIK-UHFFFAOYSA-N		| StdInChIKey = NJGBTKGETPDVIK-UHFFFAOYSA-N
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = <!-- blanked - oldvalue: 5471-51-2 -->
			| CASNo = 5471-51-2
	| PubChem=21648
			| PubChem = 21648
	| EINECS=226-806-4
	| SMILES = O=C(CCc1ccc(O)cc1)C		| EINECS = 226-806-4
			| SMILES = O=C(CCc1ccc(O)cc1)C
			| UNII = 7QY1MH15BG
	| Abbreviations=RK
			| UNII_Ref = {{fdacite|correct|FDA}}
	}}
			| Abbreviations = RK
	|Section2= {{Chembox Properties
			}}
	| C=10|H=12|O=2
			|Section2={{Chembox Properties
	| Appearance=White needles<ref>{{cite journal | doi = 10.1016/S0015-6264(78)80113-8 | author = Opdyke, D. L. J. | title = 4-(p-Hydroxyphenyl)-2-butanone | journal = Fd. Cosmet. Toxicol. | year = 1978 | volume = 16 | pages = 781–782}}</ref>
			| C=10|H=12|O=2
	| Density=
			| Appearance=White needles<ref name="DoiS">{{cite journal |doi=10.1016/S0015-6264(78)80113-8 |title=4-(''p''-Hydroxyphenyl)-2-butanone |year=1978 |journal=] |volume=16 |pages=781–2}}</ref>
	| MeltingPt=82-84 °C
			| Density=
	| BoilingPt=140-146 °C
			| MeltingPtC = 82 to 84
	| Boiling_notes=at 0.5 mmHg
	| Solubility=
			| BoilingPtC = 140 to 146
	}}
			| BoilingPt_notes=at 0.5&nbsp;mmHg
	|Section3= {{Chembox Hazards
			| Solubility=
	| MainHazards=
			}}
	| FlashPt=
			|Section3={{Chembox Hazards
	| Autoignition=
			| MainHazards=
	| RPhrases= {{R22}}
			| FlashPt=
	}}
			| AutoignitionPt =
			| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|302}}
			| PPhrases = {{P-phrases|264|270|301+312|330|501}}
			}}
	}}		}}
			'''Raspberry ketone''' is a ]ic compound that is the primary ] of ].
			==Occurrence==
			Raspberry ] occurs in a variety of fruits, including raspberries, ], and ].<ref>{{cite web|url=http://www.chm.bris.ac.uk/motm/raspberry-ketone/rkh.htm |title=Raspberry Ketone, Molecule of the Month |publisher=University of Bristol}}</ref> It is detected and released by orchid flowers, e.g. ''Dendrobium superbum'' (syn ''D. anosmum''),<ref>{{cite journal|last1=Nishida |first1=R. |last2=Iwahashi |first2=I. |last3=Tan |first3=K.H. |date=1993 |title=Accumulation of ''Dendrobium'' (Orchidaceae) flower fragrance in the rectal glands by males of the melon fly, ''Dacus cucurbitae'' (Tephritidae) |journal=Journal of Chemical Ecology |volume=19 |pages=713–722 |doi=10.1007/BF00985003}}</ref> and several ''Bulbophyllum'' species<ref>{{cite journal|last2=Nishida |first2=R. |last1=Tan |first1=K.H. |date=2005 |title=Synomone or Kairomone? - ''Bulbophyllum apertum'' (Orchidaceae) flower releases raspberry ketone to attract ''Bactrocera'' fruit flies |journal=Journal of Chemical Ecology |volume=31 |number=3 |pages=509–519 |doi=10.1007/s10886-005-2023-8}}</ref><ref>{{cite journal|last1=Tan |first1=K.H. |last2=Tan |first2=L.T. |date=2018 |title=Movements of floral parts and roles of the tooth on column wall of ''Bulbophyllum praetervisum'' (Orchidaceae) flower for pollination by Dacini fruit flies (Diptera: Tephritidae) |journal=Journal of Pollination Ecology |volume=24 |number=17 |pages=157–163 |doi=10.26786/1920-7603(2018)19|doi-access=free }}</ref><ref>{{cite journal|last1=Nakahira |first1=M. |last2=Ono |first2=H. |last3=Wee |first3=S.L. |last4=Nishida |first4=R. |date=2018 |title=Floral synomone diversification of ''Bulbophyllum'' sibling species (Orchidaceae) in attracting fruit fly pollinators |journal=Biochemical Systematics and Ecology |volume=81 |pages=86–95 |doi=10.1016/j.bse.2018.10.002|hdl=2433/235528 |hdl-access=free }}</ref> to attract raspberry ketone-responsive male Dacini fruit flies. It is ] from ].<ref>{{cite web |url=http://biocyc.org/META/new-image?type=PATHWAY&object=PWY-5393 |title=MetaCyc Pathway: raspberry ketone biosynthesis |publisher=] |accessdate=2012-07-12}}</ref> It can be extracted from the fruit, yielding about 1–4&nbsp;mg per kg of raspberries.<ref name=Beekwilder/>
			==Preparation==
			Since the natural abundance of raspberry ketone is very low, it is prepared industrially by a variety of methods from chemical intermediates.<ref>{{cite journal |doi=10.1021/jo00099a017 |title=Cation-Exchanged Montmorillonite-Catalyzed Facile Friedel-Crafts Alkylation of Hydroxy and Methoxy Aromatics with 4-Hydroxybutan-2-one to Produce Raspberry Ketone and Some Pharmaceutically Active Compounds |year=1994 |last1=Tateiwa |first1=Jun-Ichi |last2=Horiuchi |first2=Hiroki |last3=Hashimoto |first3=Keiji |last4=Yamauchi |first4=Takayoshi |last5=Uemura |first5=Sakae |journal=The Journal of Organic Chemistry |volume=59 |issue=20 |pages=5901–4}}</ref> One of the ways this can be done is through a ] followed by ]. First, ] is condensed with ] to form an ]. Then the ] part is reduced to the ]. This two-step method produces raspberry ketone in 99% yield.<ref>{{cite journal |doi=10.1007/s00897960034a |title=Rheosmin ('Raspberry Ketone') and Zingerone, and Their Preparation by Crossed Aldol-Catalytic Hydrogenation Sequences |year=1996 |last1=Smith |first1=Leverett R. |journal=The Chemical Educator |volume=1 |issue=3 |pages=1–18|s2cid=94729547 }}</ref> There is a less expensive hydrogenation catalyst, ], which also demonstrates high selectivity towards hydrogenation of the double bond of ].<ref>{{cite journal |doi=10.5560/ZNB.2014-4118 |title=Synthesis of Raspberry and Ginger Ketones by Nickel Boride-catalyzed Hydrogenation of 4-Arylbut-3-en-2-ones |year=2014 |last1=Bandarenko |first1=Mikhail |last2=Kovalenko |first2=Vitaly |journal=Zeitschrift für Naturforschung B |volume=69b |issue=8 |pages=885–888|doi-access=free }}</ref>
			:]
			==Uses==
			Raspberry ketone is sometimes used in perfumery, in cosmetics, and as a food additive to impart a fruity odor. It is one of the most expensive natural flavor components used in the food industry. The natural compound can cost as much as $20,000 per kg.<ref name=Beekwilder>{{cite journal |doi=10.1002/biot.200700076 |title=Microbial production of natural raspberry ketone |year=2007 |last1=Beekwilder |first1=Jules |last2=Van Der Meer |first2=Ingrid M. |last3=Sibbesen |first3=Ole |last4=Broekgaarden |first4=Mans |last5=Qvist |first5=Ingmar |last6=Mikkelsen |first6=Joern D. |last7=Hall |first7=Robert D. |journal=Biotechnology Journal |volume=2 |issue=10 |pages=1270–9 |pmid=17722151|s2cid=32088996 }}</ref>
			==Marketing==
			Although products containing this compound are marketed for weight loss, there is no clinical evidence for this effect in humans.<ref name=webmd>{{cite web |url=https://www.webmd.com/diet/raspberry-ketones-uses-risks |title=Raspberry Ketones: Uses, Health Benefits, and Risks |publisher=]}}</ref><ref name=webmd2>
			{{cite web |url=https://www.webmd.com/vitamins/ai/ingredientmono-1262/raspberry-ketone |title=Raspberry Ketone |publisher=]}}</ref> They are called "ketones" because of the ] (acetone) group at their end, which is shared with ].
			==Safety==
			Little is known about the long-term safety of raspberry ketone supplements,<ref name=Bredsdorff >{{cite journal | journal = Regul Toxicol Pharmacol | date = 2015 | volume = 73 | issue = 1 | pages = 196–200 | doi = 10.1016/j.yrtph.2015.06.022 | title = Raspberry ketone in food supplements - High intake, few toxicity data - A cause for safety concern? |vauthors=Bredsdorff L, Wedebye EB, Nikolov NG, Hallas-Møller T, Pilegaard K | pmid = 26160596 | s2cid = 38312188 }}</ref><ref>{{cite web | url = http://altmedicine.about.com/od/weight_Loss/a/Raspberry-Ketones-Weight-Loss.htm | title = Raspberry Ketones for Weight Loss | author = Cathy Wong | publisher = About.com}}</ref> especially since little research has been done with humans.<ref name=Canberra>{{cite web|last1=Canberra|first1=Jules|title=What's All The Hype About Raspberry Ketone?|url=https://www.authorityhealth.com/raspberry-ketone-benefits|website=Authority Health|accessdate=30 October 2017}}</ref> Toxicological models indicate a potential for ] effects, as well as effects on reproduction and development.<ref name=Bredsdorff/> Furthermore, in many ]s containing raspberry ketones, manufacturers add other ingredients such as ] which may have unsafe effects.<ref name=Canberra/>
			In 1965, the US ] classified raspberry ketone as ] (GRAS) for the small quantities used to flavor foods.<ref name="DoiS" />
			==See also==
			*]
			== References ==
			{{reflist}}
			{{Authority control}}
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