30/1/2015

RaspberryketoneWikipedia,thefreeencyclopedia

Raspberryketone
FromWikipedia,thefreeencyclopedia

Raspberryketoneisanaturalphenolic
compoundthatistheprimaryaromacompound
ofredraspberries.

Raspberryketone[1]

Contents
1Occurrence

IUPACname

2Preparation

4(4Hydroxyphenyl)butan2one

3Uses
Othernames

4Putativehealtheffects
5Safety
6References

pHydroxybenzylacetone4(pHydroxyphenyl)2butanone
FrambinoneOxyphenylonRheosminRasketone

Identifiers

Occurrence
Raspberryketoneoccursinavarietyoffruits
includingraspberries,cranberriesand
blackberries.[3]Itisbiosynthesizedfrom
coumaroylCoA.[4]Extractionofpure
raspberryketoneisusually14mgperkgof
raspberries.[5]

Preparation
Sincethenaturalabundanceofraspberry
ketoneisverylow,itispreparedindustrially
byavarietyofmethodsfromchemical
intermediates.[6]Oneofthewaysthiscanbe
doneisthroughacrossedaldolcatalytic
hydrogenation.Inacetoneandsodium
hydroxide,4hydroxybenzaldehydecanform
the,unsaturatedketone.Thisthengoes
throughcatalytichydrogenationtoproduce
raspberryketone.Thismethodproducesa99%
yield.[7]

Uses
http://en.wikipedia.org/wiki/Raspberry_ketone

Abbreviations RK
CASnumber 5471512
PubChem

21648

ChemSpider 20347
UNII

7QY1MH15BG

ECnumber

2268064

ChEBI

CHEBI:68656

ChEMBL

CHEMBL105912

Jmol3D
images

Image1
(http://chemapps.stolaf.edu/jmol/jmol.php?
model=O%3DC%28CCc1ccc%28O%29cc1%29C)
SMILES
InChI

Properties
Molecular
formula

C10H12O2

Molarmass

164.20gmol1

Appearance

Whiteneedles[2]

Meltingpoint 82to84C(180to183F355to357K)
Boilingpoint 140to146C(284to295F413to419K)at
0.5mmHg
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Raspberryketoneisusedinperfumery,in
cosmetics,andasafoodadditivetoimparta
fruityodor.Itisoneofthemostexpensive
naturalflavorcomponentsusedinthefood
industry.Thenaturalcompoundcancostas
muchas$20,000perkg.[5]Syntheticraspberry
ketoneischeaper,withestimatesrangingfrom
acoupleofdollarsperpound[8]toonefifthof
thecostofnaturalproduct.[9]

Hazards
Rphrases

R22

Exceptwherenotedotherwise,dataaregivenformaterialsin
theirstandardstate(at25C(77F),100kPa)

(verify)(whatis: / ?)
Infoboxreferences

Putativehealtheffects
Althoughproductscontainingthiscompoundaremarketedforweightloss,thereisnoclinicalevidencefor
thiseffectinhumans.[10]Theaveragedailyintakeofdietaryraspberryketonehasbeenestimatedas
0.42mg/kg/day.[11]Earlystudiesinratslookingintothepotentialtoxicityofraspberryketonefoundno
effectsonthebodyweightofratswithdosesupto100mg/kg,238timesgreaterthantheestimatedintake
forhumansor0.01%ofbodyweight.[11]Amorerecentstudydemonstratedthatwhenmicewerefedvery
highdosesofraspberryketone,upto20g/kg,2%ofbodyweightor4761timesgreaterthanestimated
humanintake,therewasastatisticallysignificantpreventionofhighfatdietinducedelevationinbody
weight.[12]Thehighdoseeffectisreportedtostemfromthealterationoflipidmetabolism,increasing
norepinephrineinducedlipolysisandfattyacidoxidationinculturedadipocytes.[13]
NutritionalsupplementmanufacturerAndrewLessmancriticizedandcounteredsensationalizedmediaand
marketingclaimsaboutraspberryketonespurportedweightlossbenefitsandstronglycautionedagainstits
use.[14]

Safety
Littleisknownaboutthelongtermsafetyofraspberryketonesupplements.[15]In1965,theUSFoodand
DrugAdministrationplacedraspberryketoneongenerallyrecognizedassafe(GRAS)statusforthesmall
quantitiesusedasafoodadditive.[2]WhereasintheUKtherearecertainextractsthataretermed'novel'by
theFoodStandardsAgencyandsoareontheunauthorisedlist.[16]

References
1. ^CatalogofOrganicsandFineChemicals,AcrosOrganics,2004/05,page1250.
2. ^ab"4(pHydroxyphenyl)2butanone".FoodandCosmeticsToxicology16:7812.1978.doi:10.1016/S0015
6264(78)801138(https://dx.doi.org/10.1016%2FS00156264%2878%29801138).
3. ^RaspberryKetone(http://www.chm.bris.ac.uk/motm/raspberryketone/rkh.htm),MoleculeoftheMonth,
UniversityofBristol
4. ^"MetaCycPathway:raspberryketonebiosynthesis"(http://biocyc.org/META/newimage?
type=PATHWAY&object=PWY5393).MetaCyc.Retrieved20120712.
http://en.wikipedia.org/wiki/Raspberry_ketone

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5. ^abBeekwilder,JulesVanDerMeer,IngridM.Sibbesen,OleBroekgaarden,MansQvist,Ingmar
Mikkelsen,JoernD.Hall,RobertD.(2007)."Microbialproductionofnaturalraspberryketone".Biotechnology
Journal2(10):12709.doi:10.1002/biot.200700076(https://dx.doi.org/10.1002%2Fbiot.200700076).
PMID17722151(https://www.ncbi.nlm.nih.gov/pubmed/17722151).
6. ^Tateiwa,JunIchiHoriuchi,HirokiHashimoto,KeijiYamauchi,TakayoshiUemura,Sakae(1994)."Cation
ExchangedMontmorilloniteCatalyzedFacileFriedelCraftsAlkylationofHydroxyandMethoxyAromaticswith
4Hydroxybutan2onetoProduceRaspberryKetoneandSomePharmaceuticallyActiveCompounds".The
JournalofOrganicChemistry59(20):59014.doi:10.1021/jo00099a017
(https://dx.doi.org/10.1021%2Fjo00099a017).
7. ^Smith,LeverettR.(1996)."Rheosmin('RaspberryKetone')andZingerone,andTheirPreparationbyCrossed
AldolCatalyticHydrogenationSequences".TheChemicalEducator1(3):118.doi:10.1007/s00897960034a
(https://dx.doi.org/10.1007%2Fs00897960034a).
8. ^http://www.wordsonwellness.com/post/2012/06/13/WithAllDueRespecttoDrOzRaspberryKetoneisnot
aFatBurningMiracle.aspx
9. ^WhynoRaspberryKetonesat(http://www.theherbalinsider.com/archives/176)NOWFoods?,TheHerbal
Insider,accessed20130315
10. ^"RaspberryKetone"(http://www.webmd.com/vitaminssupplements/ingredientmono1262
RASPBERRY%20KETONE.aspx?activeIngredientId=1262).WebMD.
11. ^abGaunt,I.F.Sharratt,M.Colley,J.Lansdown,A.B.G.Grasso,P.(1970)."Acuteandshorttermtoxicity
ofphydroxybenzylacetoneinrats".FoodandCosmeticsToxicology8(4):34958.doi:10.1016/S0015
6264(70)803881(https://dx.doi.org/10.1016%2FS00156264%2870%29803881).PMID5489397
(https://www.ncbi.nlm.nih.gov/pubmed/5489397).
12. ^Morimoto,ChieSatoh,YurieHara,MarikoInoue,ShintaroTsujita,TakahiroOkuda,Hiromichi(2005).
"Antiobeseactionofraspberryketone".LifeSciences77(2):194204.doi:10.1016/j.lfs.2004.12.029
(https://dx.doi.org/10.1016%2Fj.lfs.2004.12.029).PMID15862604
(https://www.ncbi.nlm.nih.gov/pubmed/15862604).
13. ^Park,Kyoung(2010)."RaspberryKetoneIncreasesBothLipolysisandFattyAcidOxidationin3T3L1
Adipocytes".PlantaMedica76(15):16548.doi:10.1055/s00301249860(https://dx.doi.org/10.1055%2Fs
00301249860).PMID20425690(https://www.ncbi.nlm.nih.gov/pubmed/20425690).
14. ^"RaspberryKetoneisnotaFatBurningMiracle"(http://www.wordsonwellness.com/post/2012/06/13/With
AllDueRespecttoDrOzRaspberryKetoneisnotaFatBurningMiracle.aspx).WordsOnWellness.2012
0613.Retrieved201201017.Checkdatevaluesin:|accessdate=(help)
15. ^CathyWong."RaspberryKetonesforWeightLoss"
(http://altmedicine.about.com/od/weight_Loss/a/RaspberryKetonesWeightLoss.htm).About.com.
16. ^FSA."Unauthorisednovelfoods"(https://www.food.gov.uk/science/novel/unauthorised).food.gov.uk.

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