Trans-4,5-Epoxy-(E)-2-decenal: Difference between revisions

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{{DISPLAYTITLE:''trans''-4,5-Epoxy-(''E'')-2-decenal}}
{{Chembox
{{Chembox
| Name = ''trans''-4,5-Epoxy-(''E'')-2-decenal
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid =
| verifiedrevid =
| ImageFile =
| ImageFile = 4,5-Epoxy-2-decenal.svg
| ImageSize =
| ImageSize = 200px
| ImageAlt =
| ImageAlt =
| ImageFile2 = Trans-epoxi-decenal.png
| ImageSize2 = 200px
| ImageAlt2 = 3D model of the trans-4,5-Epoxy-(E)-2-decenal molecule.
| IUPACName =
| IUPACName =
| PIN =
| PIN =
| OtherNames = 3-​[(2R,​3R)-​3-​pentyloxiranyl]-​2E-​propenal, epoxy-2-decenal
| OtherNames = 3-[(2''R'',3''R'')-3-Pentyloxiranyl]-2''E''-propenal; Epoxy-2-decenal
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|unchecked|??}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 134454-31-2
| CASNo = 134454-31-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B9K240ZU36
| PubChem = 135338390
| PubChem = 135338390
| ChemSpiderID = 4509321
| ChemSpiderID = 4509321
Line 18: Line 25:
| SMILES = CCCCCC1OC1\C=C\C=O }}
| SMILES = CCCCCC1OC1\C=C\C=O }}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| C=10|H=16|O=2
| Formula =
| MolarMass = 168.2328 g/mol
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility = water}}
| Solubility =}}
| Section7 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord=Danger
| HPhrases = {{H-phrases|225|319|336}} EUH066
| PPhrases = {{P-phrases|210|261|264|280|303+361+353|304+340|305+351+338|312|337+313}}
}}
}}
}}
⚫
'''Trans-4,5-epoxy-(E)-2-decenal''' is an oxygenated α,β unsaturated [[aldehyde]] found in mammalian blood that gives blood its characteristic metallic odor. It is used by predators to locate blood or prey.<ref>{{cite web|url=http://phys.org/news/2014-11-odor-blood-component-powerful-trigger.html|title=Odor that smells like blood: Single component powerful trigger for large carnivores|date=11 November 2014|publisher=Physorg|accessdate=11 November 2014}}</ref> Humans can smell it at a concentration of 1.5 pg/l in air.<ref name="Lin2001">{{cite journal|last=Lin|first=Jianming|coauthors=Laurent B. Fay, Dieter H. Welti, Imre Blank|year=2001|title=Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay|journal=Lipids|volume=36|issue=7|pages=749–756|issn=0024-4201|doi=10.1007/s11745-001-0781-x}}</ref> at 15 ng/L in water and 1.3μg/L in oil.<ref name="Lin1999">{{cite journal|last=Lin|first=Jianming|coauthors=Laurent B. Fay, Dieter H. Welti, Imre Blank|year=1999|title=Synthesis of trans-4,5-epoxy-(E)-2-decenal and its deuterated analog used for the development of a sensitive and selective quantification method based on isotope dilution assay with negative chemical ionization|journal=Lipids|volume=34|issue=10|pages=1117–1126|issn=0024-4201|doi=10.1007/s11745-999-0463-8}}</ref>

⚫
'''''trans''-4,5-Epoxy-(''[[E-Z notation|E]]'')-2-decenal''' is an oxygenated α,β-unsaturated [[aldehyde]] found in mammalian blood that gives blood its characteristic metallic odor. It is used by predators to locate blood or prey.<ref>{{cite web|url=http://phys.org/news/2014-11-odor-blood-component-powerful-trigger.html|title=Odor that smells like blood: Single component powerful trigger for large carnivores|date=11 November 2014|publisher=Physorg|accessdate=11 November 2014}}</ref> Humans can smell it at a concentration of 1.5 pg/L in air,<ref name="Lin2001">{{cite journal|last=Lin|first=Jianming|author2=Laurent B. Fay |author3=Dieter H. Welti |author4=Imre Blank |year=2001|title=Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay|journal=Lipids|volume=36|issue=7|pages=749–756|issn=0024-4201|doi=10.1007/s11745-001-0781-x|pmid=11521974|s2cid=3979031}}</ref> at 15&nbsp;ng/L in water and 1.3μg/L in oil.<ref name="Lin1999">{{cite journal|last=Lin|first=Jianming|author2=Laurent B. Fay |author3=Dieter H. Welti |author4=Imre Blank |year=1999|title=Synthesis of trans-4,5-epoxy-(E)-2-decenal and its deuterated analog used for the development of a sensitive and selective quantification method based on isotope dilution assay with negative chemical ionization|journal=Lipids|volume=34|issue=10|pages=1117–1126|issn=0024-4201|doi=10.1007/s11745-999-0463-8|pmid=10580339|s2cid=4054911}}</ref> It was permitted as a [[Flavoring#Flavorants or flavorings|food flavouring]] in the [[European Union|EU]] until it was prohibited on 11 July 2017<ref>{{cite web|title=COMMISSION REGULATION (EU) 2017/1250 of 11 July 2017 amending Annex I to Regulation (EC) No 1334/2008 of the European Parliament and of the Council as regards removal from the Union list of the flavouring substance 4,5-epoxydec-2(trans)-enal|url=http://eur-lex.europa.eu/eli/reg/2017/1250/oj|date=11 July 2017|work=Official Journal of the European Union}}</ref> on the grounds of possible genotoxicity, as observed from rat livers.<ref>{{cite journal |last1=EFSA CEF Panel |title=Scientific Opinion on Flavouring Group Evaluation 226 Revision 1 (FGE.226Rev1): consideration of genotoxicity data on one α,β-unsaturated aldehyde from chemical subgroup 1.1.1(b) of FGE.19 |journal=EFSA Journal |date=2017 |volume=15 |issue=5 |pages=4847–4871 |doi=10.2903/j.efsa.2017.4847 |pmid=32625501 |pmc=7010128 }}</ref>


⚫
It can be formed during baking fats that contain [[linoleic acid]]. 13-Hydroperoxy-9,11-octadecadienoic acid and 9-hydroperoxy-10,12-octadecadienoic acid are intermediates in the process.<ref name="Gassenmeier1994">{{cite journal|last=Gassenmeier|first=Klaus|author2=Peter Schieberle|year=1994|title=Formation of the intense flavor compoundtrans-4,5-epoxy-(E)-2-decenal in thermally treated fats|journal=Journal of the American Oil Chemists' Society|volume=71|issue=12|pages=1315–1319|issn=0003-021X|doi=10.1007/BF02541347|s2cid=85079936}}</ref> The aldehyde also forms in cooked beef when it sits in the refrigerator for too long contributing to a stale smell.<ref name="Konopka1991">{{cite journal|last=Konopka|first=Ute Christine|author2=Werner Grosch|year=1991|title=Potent odorants causing the warmed-over flavour in boiled beef|journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung|volume=193|issue=2|pages=123–125|issn=0044-3026|doi=10.1007/BF01193360|s2cid=83249703}}</ref> It is also an important part of the smell of raw and cooked [[mutton]].<ref name="Rota2005">{{cite book|last=Rota|first=Valerie|author2=Peter Schieberle|year=2005|volume=920|pages=73–83|issn=1947-5918|doi=10.1021/bk-2005-0920.ch006|chapter=Changes in Key Odorants of Sheep Meat Induced by Cooking|title=Food Lipids|series=ACS Symposium Series|isbn=0-8412-3896-0}}</ref>
It is permitted as a food flavouring in the EU.


Humans are more sensitive to the smell of ''trans''-4,5-Epoxy-(''E'')-2-decenal than mice.<ref>{{cite journal |last1=McGann |first1=John P. |title=Poor human olfaction is a 19th-century myth |journal=Science |date=11 May 2017 |volume=356 |issue=6338 |pages=eaam7263 |doi=10.1126/science.aam7263|pmid=28495701 |pmc=5512720 |doi-access=free }}</ref>
⚫
It can be formed during baking fats that contain linoleic acid. 13-hydroperoxy-9,11-octadecadienoic acid and 9-hydroperoxy-10,12-octadecadienoic acid are intermediates in the process.<ref name="Gassenmeier1994">{{cite journal|last=Gassenmeier|first=Klaus|coauthors=Peter Schieberle|year=1994|title=Formation of the intense flavor compoundtrans-4,5-epoxy-(E)-2-decenal in thermally treated fats|journal=Journal of the American Oil Chemists’ Society|volume=71|issue=12|pages=1315–1319|issn=0003-021X|doi=10.1007/BF02541347}}</ref> The aldehyde also forms in cooked beef when it sits in the refrigerator for too long contributing to a stale smell.<ref name="Konopka1991">{{cite journal|last=Konopka|first=Ute Christine|coauthors=Werner Grosch|year=1991|title=Potent odorants causing the warmed-over flavour in boiled beef|journal=Zeitschrift für Lebensmittel-Untersuchung und -Forschung|volume=193|issue=2|pages=123–125|issn=0044-3026|doi=10.1007/BF01193360}}</ref> It is also an important part of the smell of raw and cooked [[mutton]].<ref name="Rota2005">{{cite journal|last=Rota|first=Valerie|coauthors=Peter Schieberle|year=2005|title=Changes in Key Odorants of Sheep Meat Induced by Cooking|volume=920|pages=73–83|issn=1947-5918|doi=10.1021/bk-2005-0920.ch006}}</ref>


==References==
==References==
{{Reflist}}
{{Reflist|30em}}


{{DEFAULTSORT:Epoxy-(E)-2-decenal, trans-4, 5-}}
[[Category:Unsaturated compounds]]
[[Category:Unsaturated compounds]]
[[Category:Epoxides]]
[[Category:Epoxides]]
[[Category:Aldehydes]]
[[Category:Conjugated aldehydes]]

Latest revision as of 06:53, 21 September 2022

trans-4,5-Epoxy-(E)-2-decenal
3D model of the trans-4,5-Epoxy-(E)-2-decenal molecule.
Names
Other names
3-[(2R,3R)-3-Pentyloxiranyl]-2E-propenal; Epoxy-2-decenal
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C10H16O2/c1-2-3-4-6-9-10(12-9)7-5-8-11/h5,7-10H,2-4,6H2,1H3/b7-5+/t9-,10+/m0/s1
    Key: HIOMEXREAUSUBP-FNORWQNLSA-N
  • CCCCCC1OC1\C=C\C=O
Properties
C10H16O2
Molar mass 168.236 g·mol−1
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H319, H336 EUH066
P210, P261, P264, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

trans-4,5-Epoxy-(E)-2-decenal is an oxygenated α,β-unsaturated aldehyde found in mammalian blood that gives blood its characteristic metallic odor. It is used by predators to locate blood or prey.[1] Humans can smell it at a concentration of 1.5 pg/L in air,[2] at 15 ng/L in water and 1.3μg/L in oil.[3] It was permitted as a food flavouring in the EU until it was prohibited on 11 July 2017[4] on the grounds of possible genotoxicity, as observed from rat livers.[5]

It can be formed during baking fats that contain linoleic acid. 13-Hydroperoxy-9,11-octadecadienoic acid and 9-hydroperoxy-10,12-octadecadienoic acid are intermediates in the process.[6] The aldehyde also forms in cooked beef when it sits in the refrigerator for too long contributing to a stale smell.[7] It is also an important part of the smell of raw and cooked mutton.[8]

Humans are more sensitive to the smell of trans-4,5-Epoxy-(E)-2-decenal than mice.[9]

References[edit]

  1. ^ "Odor that smells like blood: Single component powerful trigger for large carnivores". Physorg. 11 November 2014. Retrieved 11 November 2014.
  2. ^ Lin, Jianming; Laurent B. Fay; Dieter H. Welti; Imre Blank (2001). "Quantification of key odorants formed by autoxidation of arachidonic acid using isotope dilution assay". Lipids. 36 (7): 749–756. doi:10.1007/s11745-001-0781-x. ISSN 0024-4201. PMID 11521974. S2CID 3979031.
  3. ^ Lin, Jianming; Laurent B. Fay; Dieter H. Welti; Imre Blank (1999). "Synthesis of trans-4,5-epoxy-(E)-2-decenal and its deuterated analog used for the development of a sensitive and selective quantification method based on isotope dilution assay with negative chemical ionization". Lipids. 34 (10): 1117–1126. doi:10.1007/s11745-999-0463-8. ISSN 0024-4201. PMID 10580339. S2CID 4054911.
  4. ^ "COMMISSION REGULATION (EU) 2017/1250 of 11 July 2017 amending Annex I to Regulation (EC) No 1334/2008 of the European Parliament and of the Council as regards removal from the Union list of the flavouring substance 4,5-epoxydec-2(trans)-enal". Official Journal of the European Union. 11 July 2017.
  5. ^ EFSA CEF Panel (2017). "Scientific Opinion on Flavouring Group Evaluation 226 Revision 1 (FGE.226Rev1): consideration of genotoxicity data on one α,β-unsaturated aldehyde from chemical subgroup 1.1.1(b) of FGE.19". EFSA Journal. 15 (5): 4847–4871. doi:10.2903/j.efsa.2017.4847. PMC 7010128. PMID 32625501.
  6. ^ Gassenmeier, Klaus; Peter Schieberle (1994). "Formation of the intense flavor compoundtrans-4,5-epoxy-(E)-2-decenal in thermally treated fats". Journal of the American Oil Chemists' Society. 71 (12): 1315–1319. doi:10.1007/BF02541347. ISSN 0003-021X. S2CID 85079936.
  7. ^ Konopka, Ute Christine; Werner Grosch (1991). "Potent odorants causing the warmed-over flavour in boiled beef". Zeitschrift für Lebensmittel-Untersuchung und -Forschung. 193 (2): 123–125. doi:10.1007/BF01193360. ISSN 0044-3026. S2CID 83249703.
  8. ^ Rota, Valerie; Peter Schieberle (2005). "Changes in Key Odorants of Sheep Meat Induced by Cooking". Food Lipids. ACS Symposium Series. Vol. 920. pp. 73–83. doi:10.1021/bk-2005-0920.ch006. ISBN 0-8412-3896-0. ISSN 1947-5918.
  9. ^ McGann, John P. (11 May 2017). "Poor human olfaction is a 19th-century myth". Science. 356 (6338): eaam7263. doi:10.1126/science.aam7263. PMC 5512720. PMID 28495701.
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