Citral

Citral
	IUPAC name 3,7-dimethylocta-2,6-dienal
	Other names citral; geranial; neral; geranialdehyde
Identifiers
CAS number	5392-40-5
PubChem	638011
ChemSpider	553578
UNII	T7EU0O9VPP
KEGG	C01499
ChEBI	CHEBI:16980
ChEMBL	CHEMBL1080997
RTECS number	RG5075000
Jmol-3D images	Image 1; Image 2
	SMILES O=CC=C(C)CCC=C(C)C O=C/C=C(/CC/C=C(/C)C)C ;
	InChI InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+ ; Key: WTEVQBCEXWBHNA-JXMROGBWSA-N InChI=1/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+; Key: WTEVQBCEXWBHNA-JXMROGBWBB ;
Properties
Molecular formula	C10H16O
Molar mass	152.24 g/mol
Appearance	Pale yellow liquid
Odor	Lemon like
Density	0.893 g/cm³
Boiling point	229 °C, 502 K, 444 °F
Hazards
R-phrases	R36, R37, R38
NFPA 704	1 0 0
Flash point	91 °C
Related compounds
Related alkenals	Citronellal; Methacrolein; trans-2-Methyl-2-butenal
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

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Citral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either of, or a mixture of, a pair 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.

[edit] 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]

[edit] Uses

Geranial has a strong lemon 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, and to mask the smell of smoke.

[edit] Health and safety information

Citral should be avoided by people with perfume allergies.^[8]

[edit] Compendial status

British Pharmacopoeia ^[9]

[edit] See also

[edit] References

^ Citral, The Merck Index, 12th Edition.
^ Fenaroli, G., Furia, T.E., Bellanca, N., Handbook of Flavor Ingredients, ISBN 0878195327
^ Lawless, J., The Illustrated Encyclopedia of Essential Oils, ISBN 1-85230-661-0
^ The Aromatic Plant Project
^ Onawunmi, G.O. (1989). "Evaluation of the antimicrobial activity of citral". Lett. Appl. Microbial. 9 (3): 105–108. doi:10.1111/j.1472-765X.1989.tb00301.x.
^ Kuwahara, Y., Suzuki, H., Matsumoto, K. & Wada, Y. (1983). "Pheromone study on acarid mites. XI. Function of mite body as geometrical isomerization and reduction of citral (the alarm pheromone) Carpoglyphus lactis". Appl. Entomol. Zool. 18: 30–39.
^ Robacker, D.C. & Hendry, L.B. (1977). "Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor". J. Chem. Ecol. 3 (5): 563–577. doi:10.1007/BF00989077.
^ Survey and health assessment of chemical substances in massage oils
^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 31 March 2010.

[edit] External links

MSDS

[0] Citral, The Merck Index, 12th Edition.

[1] Fenaroli, G., Furia, T.E., Bellanca, N., Handbook of Flavor Ingredients, ISBN 0878195327

[2] Lawless, J., The Illustrated Encyclopedia of Essential Oils, ISBN 1-85230-661-0

[3] The Aromatic Plant Project

[4] Onawunmi, G.O. (1989). "Evaluation of the antimicrobial activity of citral". Lett. Appl. Microbial. 9 (3): 105–108. doi:10.1111/j.1472-765X.1989.tb00301.x.

[5] Kuwahara, Y., Suzuki, H., Matsumoto, K. & Wada, Y. (1983). "Pheromone study on acarid mites. XI. Function of mite body as geometrical isomerization and reduction of citral (the alarm pheromone) Carpoglyphus lactis". Appl. Entomol. Zool. 18: 30–39.

[6] Robacker, D.C. & Hendry, L.B. (1977). "Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor". J. Chem. Ecol. 3 (5): 563–577. doi:10.1007/BF00989077.

[7] Survey and health assessment of chemical substances in massage oils

[ib29-8] The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 31 March 2010.

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Citral

Contents

[edit] Occurrence

[edit] Uses

[edit] Health and safety information

[edit] Compendial status

[edit] See also

[edit] References

[edit] External links

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Citral^[1]


IUPAC name 3,7-dimethylocta-2,6-dienal
Other names citral geranial neral geranialdehyde
Identifiers
CAS number	5392-40-5^Y
PubChem	638011
ChemSpider	553578^Y
UNII	T7EU0O9VPP^Y
KEGG	C01499^Y
ChEBI	CHEBI:16980^Y
ChEMBL	CHEMBL1080997^Y
RTECS number	RG5075000
Jmol-3D images	Image 1 Image 2
SMILES O=CC=C(C)CCC=C(C)C O=C/C=C(/CC/C=C(/C)C)C
InChI InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+^Y Key: WTEVQBCEXWBHNA-JXMROGBWSA-N^Y InChI=1/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+ Key: WTEVQBCEXWBHNA-JXMROGBWBB
Properties
Molecular formula	C₁₀H₁₆O
Molar mass	152.24 g/mol
Appearance	Pale yellow liquid
Odor	Lemon like
Density	0.893 g/cm³
Boiling point	229 °C, 502 K, 444 °F
Hazards
R-phrases	R36, R37, R38
NFPA 704	1 0 0
Flash point	91 °C
Related compounds
Related alkenals	Citronellal Methacrolein trans-2-Methyl-2-butenal
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references