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C83007

Sigma-Aldrich

Citral

95%

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Synonym(s):
Lemonal, 3,7-Dimethyl-2,6-octadienal, Geranial and neral mixture
Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)=CHCHO
CAS Number:
Molecular Weight:
152.23
Beilstein:
1721871
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

5 (vs air)

Quality Level

vapor pressure

0.2 mmHg ( 200 °C)

Assay

95%

form

liquid

refractive index

n20/D 1.488 (lit.)

bp

229 °C (lit.)

density

0.888 g/mL at 25 °C (lit.)

SMILES string

[H]C(=O)C=C(C)CC\C=C(\C)C

InChI

1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3

InChI key

WTEVQBCEXWBHNA-UHFFFAOYSA-N

Gene Information

human ... CYP1A2(1544)

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General description

Citral is a mixture of neral (cis isomer of 3,7-dimethyl-2,6-octadienal) and geranial (trans isomer of 3,7-dimethyl-2,6-octadienal). It exhibits antimicrobial activity and pheromonal effects and is generally used for the synthesis of vitamin A and ionones.

Citral is a monoterpene aldehyde used as an aromatic ingredient in food and cosmetic industry.

Application

  • Citral has been used as an anti-tumor agent against breast cancer cell lines (MCF-7 and MDA-MB-231).
  • It shows antipyretic effects which can be studied by systemic administration of lipopolysaccharide (LPS) to rats.
  • It can undergo 1,3-dipolar cycloaddition reaction with trimethylsilylazide to form 1,2,3-triazolines which possess pharmaceutical properties.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

208.4 °F - DIN 51758

Flash Point(C)

98 °C - DIN 51758

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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  5. What is the apparent molarity of Citral, Products W230316, C83007, and W230308?

    The apparent molarity of a neat liquid may be calculated from the density and molecular weight.  In the case of citral, the density is 0.888 g/mL and the molecular weight is 152.23 g/mole. By writing the density as 888 g/L, the calculation is 888 g/L divided by 152.23 g/mole = 5.83 mole/L, or 5.83 M.

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Antipyretic effects of citral and possible mechanisms of action
Emilio-Silva MT, et al.
Inflammation, 40(5), 1735-1741 (2017)
Chemical and antimicrobial studies of monoterpene: Citral
Saddiq, Amna A and Khayyat, et al.
Pesticide Biochemistry and Physiology, 98, 89-93 (2010)
Citral induced apoptosis in MDA-MB-231 spheroid cells
Nigjeh SE, et al.
BMC Complementary and Alternative Medicine, 18(1), 56-56 (2018)
Theoretical and experimental studies of 1, 3-dipolar cycloaddition reactions between trimethylsilylazide and citral (geranial and neral)
Taban S and Taherpour AA
Indian Journal of Chemistry, 55(B), 1400-1414 (2016)
Ana Isabel Vieira et al.
Foods (Basel, Switzerland), 8(2) (2019-02-06)
Edible coatings supplemented with essential oil components have been investigated to control spoilage microorganisms. In this study, the survival of Listeria monocytogenes and Salmonella enterica serovar Typhimurium on apples treated with edible coatings based on sodium alginate (2%) (ECs) and

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