Chamazulene

Names

[ CAS No. ]:
529-05-5

[ Name ]:
Chamazulene

[Synonym ]:
7-Ethyl-1,4-dimethylazulene
Azulene, 7-ethyl-1,4-dimethyl-
Chamazulene
7-Ethyl-1,4-dimethylazulene Chamazulen Dimethulene

Biological Activity

[Description]:

Chamazulene, a natural compound, is an antioxidant-type inhibitor of leukotriene B4 formation[1].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Leukotriene Receptor

Research Areas >> Inflammation/Immunology

[References]

[1]. H Safayhi, et al. Chamazulene: an antioxidant-type inhibitor of leukotriene B4 formation. Planta Med. 1994 Oct;60(5):410-3.

[2]. Andrea Capuzzo, et al. Antioxidant and radical scavenging activities of chamazulene. Nat Prod Res. 2014;28(24):2321-3.

[3]. Ding Ma, et al. Chamazulene reverses osteoarthritic inflammation through regulation of matrix metalloproteinases (MMPs) and NF-kβpathway in in-vitro and in-vivo models. Biosci Biotechnol Biochem. 2020 Feb;84(2):402-410.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
299.1±20.0 °C at 760 mmHg

[ Melting Point ]:
<25℃

[ Molecular Formula ]:
C₁₄H₁₆

[ Molecular Weight ]:
184.277

[ Flash Point ]:
137.4±12.5 °C

[ Exact Mass ]:
184.125198

[ LogP ]:
5.36

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.585

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CO4780000

CHEMICAL NAME :: Azulene, 1,4-dimethyl-7-ethyl-

CAS REGISTRY NUMBER :: 529-05-5

BEILSTEIN REFERENCE NO. :: 1306577

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C14-H16

MOLECULAR WEIGHT :: 184.30

WISWESSER LINE NOTATION :: L57J B1 F1 I2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: RRESA8 Rastitel'nye Resursy. Plant Resources. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1965- Volume(issue)/page/year: 3,67,1967

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 600 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression Lungs, Thorax, or Respiration - other changes

REFERENCE :: RRESA8 Rastitel'nye Resursy. Plant Resources. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1965- Volume(issue)/page/year: 3,67,1967

Safety Information

[ Hazard Statements ]:
H413

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2902909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2902909090

[ Summary ]:
2902909090 other aromatic hydrocarbons。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:2.0%。General tariff:30.0%

Articles

Rapid evaluation and comparison of natural products and antioxidant activity in calendula, feverfew, and German chamomile extracts.

J. Chromatogr. A. 1385 , 103-10, (2015)

The present study describes a simple high performance thin layer chromatographic (HPTLC) method for the simultaneous quantification of apigenin, chamazulene, bisabolol and the use of DPPH free radical...

Chamazulene: an antioxidant-type inhibitor of leukotriene B4 formation.

Planta Med. 60(5) , 410-3, (1994)

Matricine and its transformation product chamazulene are constituents of chamomile extracts. Both have been demonstrated to exert anti-inflammatory activity in vivo. Since preparations from chamomile ...

[Pharmacologic studies on chamomile compounds. VI. Studies on the antiphlogistic effect of chamazulene and matricine].

Planta Med. 49(2) , 67-73, (1983)