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Citral

Names

[ CAS No. ]:
5392-40-5

[ Name ]:
Citral

[Synonym ]:
Lemsyn GB
3,7-Dimethyl-1,2,6-octadienal
3,7-Dimethyl-2,6-octadienal,Geranial and neral mixture
LEMAROME
2,6-octadienal, 3,7-dimethyl-
(2E)-3,7-Dimethyl-2,6-octadienal
NERAL
gerznial
lemsyngb
3,7-Dimethylocta-2,6-dienal
3,7-dimethyl-2,6-octadien-1-al
3,7-Dimethyl-2,6-octadienal
LEMSYN
GERANIAL
3,7-dimethyl-trans-2,6-octadienal
2,6-Octadienal, 3,7-dimethyl-, (2E)-
MFCD00006997
Citral
EINECS 226-394-6

Biological Activity

[Description]:

Citral is a monoterpene found in Cymbopogon citratus essential oil, with antihyperalgesic, anti-nociceptive and anti-inflammatory effects[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others
Research Areas >> Inflammation/Immunology

[References]

[1]. Campos CA, et al. Anti-hyperalgesic and anti-inflammatory effects of citral with β-cyclodextrin and hydroxypropyl-β-cyclodextrin inclusion complexes in animal models. Life Sci. 2019 Jul 15;229:139-148.

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
229.0±9.0 °C at 760 mmHg

[ Melting Point ]:
< -10ºC

[ Molecular Formula ]:
C10H16O

[ Molecular Weight ]:
152.233

[ Flash Point ]:
101.7±0.0 °C

[ Exact Mass ]:
152.120117

[ PSA ]:
17.07000

[ LogP ]:
3.17

[ Vapour density ]:
5 (vs air)

[ Vapour Pressure ]:
0.1±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.457

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. but readily isomerizes. Incompatible with alkalies, strong oxidizing agents, strong acids. Combustible. Air and light sensitive.

[ Water Solubility ]:
PRACTICALLY INSOLUBLE

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RG5075000
CHEMICAL NAME :
2,6-Octadienal, 3,7-dimethyl-
CAS REGISTRY NUMBER :
5392-40-5
BEILSTEIN REFERENCE NO. :
1721871
LAST UPDATED :
199801
DATA ITEMS CITED :
30
MOLECULAR FORMULA :
C10-H16-O
MOLECULAR WEIGHT :
152.26
WISWESSER LINE NOTATION :
VH1UY1&3Y1&U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Human
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Human - man
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Mammal - pig
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - guinea pig
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - guinea pig
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4960 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
460 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6 gm/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
2250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
24 gm/kg/10D-I
TOXIC EFFECTS :
Liver - changes in liver weight Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - hepatic microsomal mixed oxidase (dealkylation, hydroxylation, etc.) Biochemical - Effect on specific coenzyme - CoA
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14952 mg/kg/14D-I
TOXIC EFFECTS :
Liver - other changes Liver - changes in liver weight Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1250 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2500 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 gm/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
10 gm/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - sex ratio
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
DOSE :
28 gm/kg
SEX/DURATION :
female 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - oogenesis Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
DOSE :
46 gm/kg
SEX/DURATION :
female 14 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
DOSE :
46 gm/kg
SEX/DURATION :
female 14 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Fertility - other measures of fertility Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Administration onto the skin
DOSE :
27600 mg/kg
SEX/DURATION :
female 60 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1800 mg/kg
SEX/DURATION :
female 22 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - oogenesis Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1800 mg/kg
SEX/DURATION :
female 6 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Effects on Newborn - live birth index (measured after birth)

MUTATION DATA

TYPE OF TEST :
DNA repair
TEST SYSTEM :
Bacteria - Bacillus subtilis
DOSE/DURATION :
2222 ug/disc
REFERENCE :
OIGZDE Osaka-shi Igakkai Zasshi. Journal of Osaka City Medical Association. (Osaka-shi Igakkai, c/o Osaka-shiritsu Daigaku Igakubu, 1-4-54 Asahi-cho, Abeno-ku, Osaka, 545, Japan) V.24- 1975- Volume(issue)/page/year: 34,267,1985 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83184 No. of Facilities: 353 (estimated) No. of Industries: 5 No. of Occupations: 33 No. of Employees: 68051 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83184 No. of Facilities: 12505 (estimated) No. of Industries: 98 No. of Occupations: 84 No. of Employees: 200484 (estimated) No. of Female Employees: 83180 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H317-H319

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R38;R43

[ Safety Phrases ]:
S24/25-S37

[ RIDADR ]:
1760

[ WGK Germany ]:
1

[ RTECS ]:
RG5075000

[ Packaging Group ]:
III

[ Hazard Class ]:
8

[ HS Code ]:
2932999099

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2912190090

[ Summary ]:
2912190090 acyclic aldehydes without other oxygen function。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

Two types of alcohol dehydrogenase from Perilla can form citral and perillaldehyde.

Phytochemistry 104 , 12-20, (2014)

Studies on the biosynthesis of oil compounds in Perilla will help in understanding regulatory systems of secondary metabolites and in elucidating reaction mechanisms for natural product synthesis. In ...

Heterogeneous nucleation and shape transformation of multicomponent metallic nanostructures.

Nat. Mater. 14(2) , 215-23, (2015)

To be able to control the functions of engineered multicomponent nanomaterials, a detailed understanding of heterogeneous nucleation at the nanoscale is essential. Here, by using in situ synchrotron X...

Effect of citral on the cytotoxicity of doxorubicin in human B-lymphoma cells.

Pharm. Biol. 53(2) , 262-8, (2015)

Doxorubicin is a chemotherapy agent used in non-Hodgkin's lymphoma but side effects limit its use. Citral is a mixture of neral and geranial found in essential oils of lemon grass.We evaluated the act...


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Related Compounds