| Revision as of 04:41, 12 February 2011 editAmirobot (talk | contribs)56,602 editsm r2.7.1) (robot Adding: es:Damascenona← Previous edit |
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{{distinguish|Damascone}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 396323746 |
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| Watchedfields = changed |
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|Name=''beta''-Damascenone'' |
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| verifiedrevid = 413428485 |
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|ImageFile=damascenone.png |
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| Name=''beta''-Damascenone |
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|ImageSize=200px |
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| ImageFile=damascenone.png |
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|IUPACName=(''E'')-1-(2,6,6-Trimethyl-1-cyclohexa-1,3-dienyl)but-2-en-1-one |
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| ImageSize=200px |
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|OtherNames= |
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| ImageFile2=Damascenone-3D.png |
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| ImageSize2=200px |
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| IUPACName=(''E'')-1-(2,6,6-Trimethyl-1-cyclohexa-1,3-dienyl)but-2-en-1-one |
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| OtherNames= |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4517997 |
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| ChemSpiderID = 4517997 |
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| InChI = 1/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ |
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| InChI = 1/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ |
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| InChIKey = POIARNZEYGURDG-FNORWQNLBV |
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| InChIKey = POIARNZEYGURDG-FNORWQNLBV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ |
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| StdInChI = 1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = POIARNZEYGURDG-FNORWQNLSA-N |
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| StdInChIKey = POIARNZEYGURDG-FNORWQNLSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=23726-93-4 |
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| CASNo=23726-93-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=5366074 |
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| UNII = U66V25TBO0 |
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| SMILES = O=C(\C1=C(\C=C/CC1(C)C)C)/C=C/C |
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| PubChem=5366074 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 67251 |
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| SMILES = O=C(\C1=C(\C=C/CC1(C)C)C)/C=C/C |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=13 |
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| Formula=C<sub>13</sub>H<sub>18</sub>O |
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| H=18 |
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| MolarMass=190.28 g/mol |
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| Appearance= |
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| O=1 |
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| Appearance= |
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| Density= |
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}} |
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}} |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| FlashPt= |
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| AutoignitionPt = |
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}} |
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}} |
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'''Damascenones''' are a series of closely related chemical compounds that are components of a variety of ]s. The damascenones belong to a family of chemicals known as rose ]s, which also includes ]s and ]s. ''beta''-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery.<ref>, John C. Leffingwell</ref> |
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'''Damascenones''' are a series of closely related chemical compounds that are components of a variety of ]s. The damascenones belong to a family of chemicals known as rose ]s, which also includes ]s and ]s. ''beta''-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery.<ref>, John C. Leffingwell</ref> |
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The damascenones are derived from the degradation of ]s. <ref>{{cite journal |
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The damascenones are derived from the degradation of ]s.<ref>{{cite journal |
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| title = The Synthesis of Damascenone and beta-Damascone and the possible mechanism of their formation from carotenoids |
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| title = The Synthesis of Damascenone and beta-Damascone and the possible mechanism of their formation from carotenoids |
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| author = Sachihiko Isoe, Shigeo Katsumura, Takeo Sakan |
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| author = Sachihiko Isoe |
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| author2 = Shigeo Katsumura |
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| author3 = Takeo Sakan |
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| journal = Helvetica Chimica Acta |
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| journal = Helvetica Chimica Acta |
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| volume = 56 |
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| volume = 56 |
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| url = |
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| doi = 10.1002/hlca.19730560508 }}</ref> |
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| doi = 10.1002/hlca.19730560508 }}</ref> |
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In 2008, (E)-β-damascenone was identified as a primary odorant in ].<ref>{{cite journal |
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| title = Characterization of the Most Odor-Active Compounds in an American Bourbon Whisky by Application of the Aroma Extract Dilution Analysis |
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| author = LUIGI POISSON |
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| author2 = PETER SCHIEBERLE |
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| journal = Journal of Agricultural and Food Chemistry |
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| volume = 56 |
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| issue = 14 |
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| pages = 5813–5819 |
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| year = 2008 |
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| doi = 10.1021/jf800382m | pmid = 18570373 |
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}}</ref> |
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==Biosynthesis== |
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{{Technical|section|date=May 2016}} |
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The biosynthesis for β-damascenone begins with ] (FPP) and ] (IPP) reacting to produce ] (GGPP) Figure 1. ]Next two molecules of GGPP are condensed together to produce ] by removal of diphosphate and a proton shift catalyzed by the enzyme ] (PSY). Phytoene then goes through a series of desaturation reactions using the enzyme ] (PDS) to produce ] then ]. Other enzymes have been found to catalyze this reaction including CrtI and CrtP.<ref>{{cite journal |
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| title = BCarotenoids and their cleavage products: Biosynthesis and functions |
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| author = Michael H. Walter |
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| author2 = Dieter Strack |
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| journal = Nat. Prod. Rep. |
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| volume = 28 |
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| issue = 4 |
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| pages = 663–692 |
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| year = 2011 |
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| doi = 10.1039/c0np00036a | pmid = 21321752 |
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}}</ref> |
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The next series of desaturation reactions is catalyzed by the enzyme ] (ZDS) to produce ] followed by ]. Other enzymes that are able to catalyze this reaction include CtrI and CrtQ. Next lycopene goes through two cyclization reactions with the use of the enzyme ] first producing ] followed by the second cyclization producing ] as shown in Figure 2.] The mechanism for the cyclization of lycopene to β-carotene is shown in Scheme 2. |
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] Next β-carotene reacts with O2 and the enzyme β-carotene ring hydroxylase producing ].<ref>{{cite journal |
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| title = The lycopene β-cyclase plays a significant role in provitamin A biosynthesis in wheat endosperm |
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| author = Jian Zeng |
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| author2 = Cheng Wang |
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| author3 = Xi Chen |
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| author4 = Mingli Zang |
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| author5 = Cuihong Yuan |
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| author6 = Xiatian Wang |
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| author7 = Qiong Wang |
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| author8 = Miao Li |
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| author9 = Xiaoyan Li |
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| author10 = Ling Chen |
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| author11 = Kexiu Li |
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| author12 = Junli Chang |
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| author13 = Yuesheng Wang |
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| author14 = Guangxia Yang |
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| author15 = Guangyuan He |
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| journal = BMC Plant Biology |
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| volume = 15 |
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| issue = 112 |
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| pages =112 |
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| year = 2015 |
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| doi = 10.1186/s12870-015-0514-5 | pmid = 25943989 |
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| pmc = 4433027 |
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| doi-access = free |
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}}</ref> |
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Zeaxanthin then reacts with O2, NADPH (H+), and reduced ferredoxin cluster in the presence of the enzyme ] (ZE) to produce antheraxanthin which reacts in a similar fashion to produce ]. Violaxanthin then reacts with the enzyme ] to form ] the main precursor for β-damascenone as shown in Figure 3.]<ref>{{cite journal |
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| title = Biosynthetic Pathway and Health Benefits of Fucoxanthin, an Algae-Specific Xanthophyll in Brown Seaweeds |
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| author = Koji Mikami |
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| author2 = Masashi Hosokawa |
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| journal = Int. J. Mol. Sci. |
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| volume = 14 |
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| issue = 7 |
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| pages = 13763–13781 |
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| year = 2013 |
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| pmc = 3742216 |
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| doi = 10.3390/ijms140713763 |
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| pmid=23820585| doi-access = free |
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}}</ref> |
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In order to generate β-damascenone from neoxanthin there are a few more modifications needed. First neoxanthin undergoes an oxidative cleavage to create the grasshopper ketone. The grasshopper ketone then undergoes a reduction to generate the allenic triol. At this stage there are two main pathways the allenic triol can take to produce the final product. The allenic triol can undergo a dehydration reaction to generate either the acetylenic diol or the allenic diol. Finally one last dehydration reaction of either the acetylenic diol or the allenic diol produces the final product β-damascenone as shown in Figure 4.]<ref>{{cite journal |
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|title=Thermal Oxidation of 9'-cis-Neoxanthin in a Model System Containing Peroxyacetic Acid Leads to Potent Odorant β-Damascenone |
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|author=Yair Bezman |
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|author2=Itzhak Bilkis |
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|author3=Peter Winterhalter |
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|author4=Peter Fleischmann |
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|author5=Russell L. Rouseff |
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|author6=Susanne Baldermann |
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|author7=Michael Naim |
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|journal= Journal of Agricultural and Food Chemistry |
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|volume=53 |
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|issue=23 |
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|pages=9199–9206 |
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|year=2005 |
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|pmid=16277423 |
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|doi=10.1021/jf051330b |
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}}</ref><ref>{{cite book |
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| title = Carotenoid Cleavage Products |
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| author = Peter Winterhalter |
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| author2 = Recep Gök |
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| volume = 1134 |
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| pages =125–137 |
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| year = 2013 |
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| doi = 10.1021/bk-2013-1134.ch011 | series = ACS Symposium Series |
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| isbn = 978-0-8412-2778-1 |
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| chapter = TDN and β-Damascenone: Two Important Carotenoid Metabolites in Wine |
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}}</ref> The proposed mechanism for the conversion of the allenic triol to the acetylenic diol is shown in Scheme 3.] The proposed mechanism for the conversion of the acetylenic diol to the final product is shown in Scheme 4.] This mechanism is known as a ]. |
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==See also== |
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==See also== |
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