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词条 Citral
释义

  1. Occurrence

  2. Uses

  3. Health and safety information

  4. See also

  5. References

  6. External links

{{chembox
| Watchedfields = changed
| verifiedrevid = 443528330
| Reference = [1]
| Name = Citral
| ImageFile = Geranial_svg.svg
| ImageAlt = Skeletal formula of geranial
| ImageCaption = Geranial
| ImageFile1 = Geranial 3D ball.png
| ImageAlt1 = Ball-and-stick model of the geranial molecule
| ImageFile2 = Neral_svg.svg
| ImageAlt2 = Skeletal formula of neral
| ImageCaption2 = Neral
| ImageFile3 = Neral-3D-balls.png
| ImageAlt3 = Ball-and-stick model of the neral molecule
| IUPACName = 3,7-dimethylocta-2,6-dienal
| OtherNames = citral
geranialdehyde
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 6327
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16980
| SMILES = O=CC=C(C)CCC=C(C)C
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 553578
| PubChem = 638011
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = T7EU0O9VPP
| InChI = 1/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+
| InChIKey = WTEVQBCEXWBHNA-JXMROGBWBB
| SMILES1 = O=C/C=C(/CC/C=C(/C)C)C
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1080997
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WTEVQBCEXWBHNA-JXMROGBWSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 5392-40-5
| RTECS = RG5075000
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01499
|Section2={{Chembox Properties
| Formula = C10H16O
| MolarMass = 152.24 g/mol
| Appearance = Pale yellow liquid
| Odor = Lemon like
| Density = 0.893 g/cm3
| VaporPressure = 0.22{{nbsp}}mmHg (20{{nbsp}}°C)
| Solubility =
| MeltingPt =
| BoilingPtC = 229
| pKa =
| MagSus = −98.9×10−6 cm3/mol
|Section3={{Chembox Structure
| Dipole =
|Section7={{Chembox Hazards
| NFPA-H = 0 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S =
| RPhrases = {{R36}}, {{R37}}, {{R38}}
| SPhrases =
| FlashPtC = 91
|Section8={{Chembox Related
| OtherFunction_label = alkenals
| OtherFunction = {{ubl
| Citronellal
| Methacrolein
| trans-2-Methyl-2-butenal
| OtherCompounds =
}}

Citral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either a pair, or a mixture of terpenoids with the molecular formula C10H16O. The two compounds are double bond isomers. The E-isomer is known as geranial or citral A. The Z-isomer is known as neral or citral B.

Occurrence

Citral is present in the oils of several plants, including lemon myrtle (90–98%), Litsea citrata (90%), Litsea cubeba (70–85%), lemongrass (65–85%), lemon tea-tree (70–80%), Ocimum gratissimum (66.5%), Lindera citriodora (about 65%), Calypranthes parriculata (about 62%), petitgrain (36%), lemon verbena (30–35%), lemon ironbark (26%), lemon balm (11%), lime (6–9%), lemon (2–5%), and orange.[2][3][4]

Uses

Geranial has a strong lemon (citrus) odor. Neral's lemon odor is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It also has strong antimicrobial qualities,[5] and pheromonal effects in insects.[6][7]

Citral is used in the synthesis of vitamin A, ionone, and methylionone, to mask the smell of smoke.

Health and safety information

Two studies showed 1–1.7% of people to be allergic to citral, with allergies frequently reported.{{cn|date=July 2018}} Citral on its own is strongly sensitizing to allergies; the International Fragrance Association recommends that citral only be used in association with substances that prevent a sensitizing effect.{{cn|date=July 2018}} Citral has been extensively tested, with no known genotoxicity or carcinogenic effect.[8]

See also

  • Citronellal
  • Geraniol
  • Limonene
  • Nerol
  • Vaporizer

References

1. ^Citral, The Merck Index, 12th Edition.
2. ^Fenaroli, G., Furia, T.E., Bellanca, N., Handbook of Flavor Ingredients, {{ISBN|0-87819-532-7}}
3. ^Lawless, J., The Illustrated Encyclopedia of Essential Oils, {{ISBN|1-85230-661-0}}
4. ^The Aromatic Plant Project
5. ^{{cite journal | author = Onawunmi, G.O. |year=1989 | title=Evaluation of the antimicrobial activity of citral |journal=Lett. Appl. Microbiol. | volume=9 |pages=105–108 | doi = 10.1111/j.1472-765X.1989.tb00301.x | issue = 3}}
6. ^{{cite journal | author = Kuwahara, Y., Suzuki, H., Matsumoto, K. & Wada, Y. |year=1983 |title=Pheromone study on acarid mites. XI. Function of mite body as geometrical isomerization and reduction of citral (the alarm pheromone) Carpoglyphus lactis |journal=Appl. Entomol. Zool. |volume=18 |pages=30–39}}
7. ^{{cite journal |author1=Robacker, D.C. |author2=Hendry, L.B. |year=1977 |title=Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor | journal=J. Chem. Ecol. |volume=3 |pages=563–577 | doi = 10.1007/BF00989077 | issue = 5}}
8. ^Survey and health assessment of chemical substances in massage oils {{webarchive|url=https://web.archive.org/web/20070628145403/http://www2.mst.dk/udgiv/publications/2006/87-7052-278-2/html/kap07_eng.htm |date=28 June 2007 }}

External links

  • MSDS
{{Use dmy dates|date=January 2011}}

4 : Flavors|Perfume ingredients|Monoterpenes|Aldehydes

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