Geranial

Citral

Geranial
Neral
Names
IUPAC name 3,7-dimethylocta-2,6-dienal
Other names citral geranialdehyde
Identifiers
CAS Number	5392-40-5 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:16980 Y
ChemSpider	553578 Y
ECHA InfoCard	100.023.994
IUPHAR/BPS	6327
KEGG	C01499 Y
PubChem CID	638011
RTECS number	RG5075000
UNII	T7EU0O9VPP Y
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
SMILES O=CC=C(C)CCC=C(C)C O=C/C=C(/CC/C=C(/C)C)C
Properties
Chemical formula	C10H16O
Molar mass	152.24 g/mol
Appearance	Pale yellow liquid
Odor	Lemon like
Density	0.893 g/cm3
Boiling point	229 °C (444 °F; 502 K)
Vapor pressure	0.22 mmHg (20 °C)
Magnetic susceptibility (χ)	-98.9·10−6 cm3/mol
Hazards
R-phrases	R36, R37, R38
NFPA 704	1 0 0
Flash point	91 °C (196 °F; 364 K)
Related compounds
Related alkenals	Citronellal Methacrolein trans-2-Methyl-2-butenal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Methacrolein
trans-2-Methyl-2-butenal

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.

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.

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, and pheromonal effects in insects.

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