Azulene

Names

[ CAS No. ]:
275-51-4

[ Name ]:
Azulene

[Synonym ]:
Bicyclo[5.3.0]deca-2,4,6,8,10-pentaene
EINECS 205-993-6
Cyclopentacycloheptene
Azunol
Bicyclo(5.3.0)-deca-2,4,6,8,10-pentaene
MFCD00003810
Azulene
Bicyclo(5.3.0)-1,3,5,7,9-decapentaene
Bicyclo[5.3.0]decapentaene
Bicyclo[0.3.5]deca-1,3,5,7,9-pentaene
Azunamic

Biological Activity

[Description]:

Azulene (Cyclopentacycloheptene) is as an isomer of naphthalene with high anti-HIV activity. Azulene, isolated from the distillation of chamomile oil, is a scaffold in medicinal chemistry[1][2][3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

[Target]

HIV

[In Vitro]

Azulene is an interesting scaffold in medicinal chemistry as it resembles several other bicyclic aromatics that are frequently found in drugs. Azulene, a structural isomer of naphthalene, is a bicyclic nonbenzenoid aromatic hydrocarbon having a dipole moment due to the electron-rich five-membered ring and electron-deficient sevenmembered ring[1].

[References]

[1]. Teppo O Leino, et al. Azulene-based Compounds for Targeting Orexin Receptors. Eur J Med Chem. 2018 Sep 5;157:88-100.

[2]. Julia Peet, et al. Antiretroviral (HIV-1) Activity of Azulene Derivatives. Bioorg Med Chem. 2016 Apr 15;24(8):1653-7.

[3]. David A. Becker, et al. A new synthesis of substituted azulenes. Journal of the American Chemical Society, 111(1), 389-391.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
220.7±7.0 °C at 760 mmHg

[ Melting Point ]:
98-100 °C(lit.)

[ Molecular Formula ]:
C₁₀H₈

[ Molecular Weight ]:
128.171

[ Flash Point ]:
76.7±8.9 °C

[ Exact Mass ]:
128.062607

[ LogP ]:
3.45

[ Vapour Pressure ]:
0.2±0.2 mmHg at 25°C

[ Index of Refraction ]:
1.632

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CO4570000

CHEMICAL NAME :: Azulene

CAS REGISTRY NUMBER :: 275-51-4

LAST UPDATED :: 199701

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C10-H8

MOLECULAR WEIGHT :: 128.18

WISWESSER LINE NOTATION :: L57J

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 180 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 520 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3 gm/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 108 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 145 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,13,1982

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 56 mg/kg

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

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#07952 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - E0278 No. of Facilities: 2232 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 20256 (estimated) No. of Female Employees: 17049 (estimated)

Safety Information

[ Symbol ]:

GHS09

[ Hazard Statements ]:
H411

[ Precautionary Statements ]:
P273

[ Personal Protective Equipment ]:
Eyeshields;Gloves

[ Hazard Codes ]:
N

[ Risk Phrases ]:
R51/53

[ Safety Phrases ]:
S61

[ RIDADR ]:
UN 3077 9/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
CO4570000

[ 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

Determination of descriptors for polycyclic aromatic hydrocarbons and related compounds by chromatographic methods and liquid-liquid partition in totally organic biphasic systems.

J. Chromatogr. A. 1361 , 240-54, (2014)

Retention factors on several columns and at various temperatures using gas chromatography and from reversed-phase liquid chromatography on a SunFire C18 column with various mobile phase compositions c...

Novel azulene-based derivatives as potent multi-receptor tyrosine kinase inhibitors.

Bioorg. Med. Chem. Lett. 20(20) , 6129-32, (2010)

A series of azulene-based derivatives were synthesized as potent inhibitors for receptor tyrosine kinases such as FMS-like tyrosine kinase 3 (FLT-3). Systematic side chain modification of prototype 1a...

Total synthesis of a CD-ring: side-chain building block for preparing 17-epi-calcitriol derivatives from the Hajos-Parrish dione.

J. Org. Chem. 76(16) , 6906-11, (2011)

An efficient synthesis of the key building block for 17-epi-calctriol from the Hajos-Parrish dione involving a sequence of diastereoselective transformation of the azulene core and the side-chain cons...