Geranial
| |
Neral
| |
Names | |
---|---|
IUPAC name
3,7-dimethylocta-2,6-dienal
| |
Other names
citral
geranialdehyde | |
Identifiers | |
3D model (
JSmol)
|
|
3DMet | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.023.994 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
RTECS number |
|
UNII | |
UN number | 2810 |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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) |
−98.9×10−6 cm3/mol | |
Hazards | |
GHS labelling: | |
Warning | |
H315, H317 | |
P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 91 °C (196 °F; 364 K) |
Related compounds | |
Related alkenals
|
|
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Citral is an acyclic monoterpene aldehyde. Being a monoterpene, it is made of two isoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; the E-isomer is named geranial (trans-citral; α-citral [2]) or citral A. The Z-isomer is named neral (cis-citral; β-citral [2]) or citral B. These stereoisomers occur as a mixture, often not in equal proportions; e.g. in essential oil of Australian ginger, the neral to geranial ratio is 0.61. [3]
Citral is present in the volatile 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. [4] [5] [6] Further, in the lipid fraction (essential oil) of Australian ginger (51–71%). [3] Of the many sources of citral, the Australian myrtaceous tree, lemon myrtle, Backhousia citriodora F. Muell. (of the family Myrtaceae), is considered superior. [7]
Citral has a strong lemon (citrus) scent and is used as an aroma compound in perfumery. It is used to fortify lemon oil. (Nerol, another perfumery compound, has a less intense but sweeter lemon note.) The aldehydes citronellal and citral are considered key components responsible for the lemon note, with citral preferred. [7]
It also has pheromonal effects in acari and insects. [8] [9]
Citral is used in the synthesis of vitamin A, lycopene, ionone and methylionone, and to mask the smell of smoke.
The herb Cymbopogon citratus has shown promising insecticidal and antifungal activity against storage pests. [10]
Citral is commonly used as a food additive ingredient. [11]
It has been tested (2016) in vitro against the food-borne pathogen Cronobacter sakazakii. [12]
In a report (1997), citral is mentioned as cytotoxic to P(388) mouse leukaemia cells. [10] It has strong antimicrobial qualities. [13]
A number of studies have shown allergic reactions to Citral. [14] The International Fragrance Association gives a no-observed-adverse-effect level of 1400 micrograms. [15] Citral has been extensively tested, with no known genotoxicity or carcinogenic effect. [16]
Geranial
| |
Neral
| |
Names | |
---|---|
IUPAC name
3,7-dimethylocta-2,6-dienal
| |
Other names
citral
geranialdehyde | |
Identifiers | |
3D model (
JSmol)
|
|
3DMet | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.023.994 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
RTECS number |
|
UNII | |
UN number | 2810 |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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) |
−98.9×10−6 cm3/mol | |
Hazards | |
GHS labelling: | |
Warning | |
H315, H317 | |
P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501 | |
NFPA 704 (fire diamond) | |
Flash point | 91 °C (196 °F; 364 K) |
Related compounds | |
Related alkenals
|
|
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Citral is an acyclic monoterpene aldehyde. Being a monoterpene, it is made of two isoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; the E-isomer is named geranial (trans-citral; α-citral [2]) or citral A. The Z-isomer is named neral (cis-citral; β-citral [2]) or citral B. These stereoisomers occur as a mixture, often not in equal proportions; e.g. in essential oil of Australian ginger, the neral to geranial ratio is 0.61. [3]
Citral is present in the volatile 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. [4] [5] [6] Further, in the lipid fraction (essential oil) of Australian ginger (51–71%). [3] Of the many sources of citral, the Australian myrtaceous tree, lemon myrtle, Backhousia citriodora F. Muell. (of the family Myrtaceae), is considered superior. [7]
Citral has a strong lemon (citrus) scent and is used as an aroma compound in perfumery. It is used to fortify lemon oil. (Nerol, another perfumery compound, has a less intense but sweeter lemon note.) The aldehydes citronellal and citral are considered key components responsible for the lemon note, with citral preferred. [7]
It also has pheromonal effects in acari and insects. [8] [9]
Citral is used in the synthesis of vitamin A, lycopene, ionone and methylionone, and to mask the smell of smoke.
The herb Cymbopogon citratus has shown promising insecticidal and antifungal activity against storage pests. [10]
Citral is commonly used as a food additive ingredient. [11]
It has been tested (2016) in vitro against the food-borne pathogen Cronobacter sakazakii. [12]
In a report (1997), citral is mentioned as cytotoxic to P(388) mouse leukaemia cells. [10] It has strong antimicrobial qualities. [13]
A number of studies have shown allergic reactions to Citral. [14] The International Fragrance Association gives a no-observed-adverse-effect level of 1400 micrograms. [15] Citral has been extensively tested, with no known genotoxicity or carcinogenic effect. [16]