Azulene

HCID 9231CAS 275-51-4

Basic information

Standard SMILES
c1ccc2cccc-2cc1
InChIKey
CUFNKYGDVFVPHO-UHFFFAOYSA-N
Molecular formula
C10H8
Average molar mass
128.17 g/mol
Monoisotopic mass
128.06260026

Overview

Azulene is a mancude carbobicyclic parent consisting of a cycloheptatriene and cyclopentadiene rings. It has a role as a volatile oil component and a plant metabolite. It is an ortho-fused bicyclic arene, a member of azulenes and a mancude carbobicyclic parent.

Names & identifiers

Preferred name
Azulene
IUPAC
azulene
English name
Azulene
Molecular formula
C10H8
Molecular weight
128.17

Names & synonyms

azulene275-51-4CyclopentacyclohepteneAzunamicBicyclo[5.3.0]decapentaeneazulenBicyclo(5.3.0)decapentaeneBicyclo(5.3.0)-deca-2,4,6,8,10-pentaene82R6M9MGLPBicyclo(5.3.0)-1,3,5,7,9-decapentaeneDTXSID2059770NSC-89248
Show more names
Azulene,99%AZULENE(RG)Azulene >AZULENE, FOR GCSoluble azulene275-51-4 AZULENEAZULENE OEKANAL
CHEBI:31249RefChem:116159DTXCID7037686205-993-6EINECS 205-993-6MFCD00003810AZULENE [MI]Azulene (JAN)

Database identifiers

CAS
275-51-4
PubChem CID
9231
DTXSID
DTXSID2059770
ChEMBL
CHEMBL3272628
ChEBI
CHEBI:31249
UNII
82R6M9MGLP
EC Number
205-993-6
Nikkaji
J39.308H

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
10

Experimental & physicochemical properties

Cosmetics · 2 items

Cosmetic ingredients (Azulene) -> CIR (Cosmetic Ingredient Review)

Soothing

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP3.22

Physicochemical properties

Melting point
98 · 98-100 °C(lit.)
Boiling point
242 °C · 242 °C(lit.)
Density
1.053 · 1.0530
refractive index
1.5736 · 1.5736 (estimate)
Flash point
241 · 241-243°C
storage temp.
2 °C · Store at +2°C to +8°C.

Safety & regulation

GHS classification

GHS Classification · 4 items

This chemical does not meet GHS hazard criteria for 9.1% (4 of 44) of reports.

H411 (90.9%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: Azulene

Azulene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesAquatic Chronic 2 (90.9%)

Toxicology

TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
Exposure RoutesOral (L10) ; inhalation (L10)
Toxicity Summary · 3 items

The CIR Expert Panel concludes that the available data are insufficient to support the safety of Azulene for use in cosmetic products.

Ingredients for which the data are insufficient and their use in cosmetics is not supported

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

Signs and SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
Carcinogen ClassificationNot listed by IARC.

Safety data

F
8
PPE
Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
CO4570000
ridadr
UN 3077 9/PG 3

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

MeSH Pharmacological Classification · 1 item

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Uses & manufacturing

Uses · 2 items

CIR ingredient: Azulene

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)

Use ClassificationCosmetics -> Soothing
General Manufacturing InformationAzulene: ACTIVE
Applications · 2 items

UsesAzulene is used as an additive in ointments. It is an active ingredient in cosmetics, shaving creams and other topicals. It is used as antioxidant and in anti-inflammatory activities. It is involved in the colorimetric determination of furfural. It acts as ligand for low valent metals and forms pi complexes with both cyclopentadienyl and cylcloheptatrienyl ligands in organometallic chemistry. It is also used as precursor for the preparation of (azulene)Mo2 (CO)6 and (azulene)Fe2 (CO)5.

Usesazulene is renowned as an anti-inflammatory, calming, and soothing agent. excellent for sensitive skin, azulene is a german chamomile derivative with a characteristic deep blue color. Careful, it stains!

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Azulene is a mancude carbobicyclic parent consisting of a cycloheptatriene and cyclopentadiene rings. It has a role as a plant metabolite and a volatile oil component. It is an ortho-fused bicyclic arene, a member of azulenes and a mancude carbobicyclic parent.

Related reactions

6 records

Linked notes

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