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Merck

C83007

Citral

95%

Synonym(s):

Lemonal, 3,7-Dimethyl-2,6-octadienal, Geranial and neral mixture

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)=CHCHO
CAS Number:
5392-40-5
Molecular Weight:
152.23
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24893046
EC Number:
226-394-6
Beilstein/REAXYS Number:
1721871
MDL number:
MFCD00006997
Assay:
95%
Form:
liquid

Key Documents

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InChI key

WTEVQBCEXWBHNA-UHFFFAOYSA-N

InChI

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

SMILES string

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

vapor density

5 (vs air)

vapor pressure

0.2 mmHg ( 200 °C)

assay

95%

form

liquid

Quality Level

100

Gene Information

human ... CYP1A2(1544)

bp

229 °C (lit.)

density

0.888 g/mL at 25 °C (lit.)

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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
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

208.4 °F - DIN 51758

flash_point_c

98 °C - DIN 51758

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Group 4: Flammable liquids + Type 3 petroleums + Hazardous rank III + Water insoluble liquid

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

C83007-5G: + C83007-VAR: + C83007-500G: + C83007-5ML: + C83007-100ML: + C83007-100G: + C83007-10L: + C83007-5KG: + C83007-500ML: + C83007-BULK:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB5304
STBK5510
STBK0532
STBJ0146
STBH8471

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Antipyretic effects of citral and possible mechanisms of action
Emilio-Silva MT, et al.
Inflammation, 40(5), 1735-1741 (2017)
Clarissa M D Mota et al.
Journal of ethnopharmacology, 250, 112486-112486 (2019-12-18)
Citral (3,7-dimethyl-2,6-octadienal) is the main component of Cymbopogon citratus (DC) Stapf, an herb with analgesic properties. Arthritic pain is the main unpleasant component of rheumatoid arthritis. The pharmacological approaches used to treat arthritic pain are often accompanied by adjuvant drugs
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)
Citral induced apoptosis in MDA-MB-231 spheroid cells
Nigjeh SE, et al.
BMC Complementary and Alternative Medicine, 18(1), 56-56 (2018)
Chemical and antimicrobial studies of monoterpene: Citral
Saddiq, Amna A and Khayyat, et al.
Pesticide Biochemistry and Physiology, 98, 89-93 (2010)
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