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
Show more names
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
- Formal charge
- 0
- Complexity
- 94.6
Experimental & physicochemical properties
Cosmetics
Cosmetic ingredients (Azulene) -> CIR (Cosmetic Ingredient Review)
Soothing
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.
- solubility
- Soluble in organic solvents.
- form
- Fine Crystalline Powder
- color
- Dark blue
- Merck
- 14 · 14,926
- BRN
- 969517 · 969517
- Henry's Law Constant
- 1.5 · 1.5×10-1 mol/(m3Pa) at 25℃, Hiatt (2013)
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- Cosmetics Ingredients Functions
- SOOTHINGSKIN CONDITIONING
- Cosmetic Ingredient Review (CIR)
- Azulene (275-51-4)
- InChI
- 1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
- InChIKey
- CUFNKYGDVFVPHO-UHFFFAOYSA-N
- SMILES
- c1ccc2cccc2cc1
- LogP
- 3.2 · 3.200
- CAS DataBase Reference
- 275 · 275-51-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-3
- FDA UNII
- 82 R6M9MGLP · 82R6M9MGLP
- EPA Substance Registry System
- Azulene (275-51-4)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 9 · GHS09
- Signal word
- Danger
- Hazard statements
- 411 · H411
- Precautionary statements
- 273 · P273-P391-P501
- PPE
- Eyeshields, Gloves
- Hazard Codes
- N
- Risk Statements
- 51 · 51/53
- Safety Statements
- 61 · 61
- RIDADR
- 3077 · UN 3077 9/PG 3
- WGK Germany
- 2 · 2
- RTECS
- 4570000 · CO4570000
- F
- 8 · 8
- TSCA
- TSCA listed
- HS Code
- 29029000 · 29029000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Aquatic Chronic 2
- Toxicity
- 50 orl-rat: · LD50 orl-rat: >4 g/kg DRUGAY 6,13,82
Safety & regulation
GHS classification
GHS Classification
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
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.
Toxicology
Toxicity Summary
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)
Safety data
- F
- 8
- PPE
- Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- CO4570000
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29029000
- Toxicity
- LD50 orl-rat: >4 g/kg DRUGAY 6,13,82
- risk_code
- 51/53
- Signal word
- Danger
- Symbol(GHS)
- GHS09
- hazard_code
- N
- safety_code
- 61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H411
- Hazard Classifications
- Aquatic Chronic 2
- Precautionary statements
- P273-P391-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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
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
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)
Applications
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
Additional notes
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
Linked notes
Loading…