chamazulene
1,4-dimethyl-7-ethylazulene
 
Notes:
Isol. as artifact from various sesquiterpene oils, e.g. from Achillea and Artemisia spp.
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CAS Number: 529-05-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 208-449-6
FDA UNII: Z439UH6E5F
Nikkaji Web: J9.436F
Beilstein Number: 1306577
MDL: MFCD00800984
XlogP3-AA: 4.40 (est)
Molecular Weight: 184.28152000
Formula: C14 H16
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance: bluish green clear liquid (est)
Assay: 97.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.98810 @  25.00 °C.
Boiling Point: 159.00 °C. @ 11.00 mm Hg
Boiling Point: 298.00 to  300.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.002000 mmHg @ 25.00 °C. (est)
Flash Point: 279.00 °F. TCC ( 137.22 °C. )
logP (o/w): 5.510
Soluble in:
 alcohol
 water, 0.2979 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
ExtraSynthese
For experimental / research use only.
Chamazulen (HPLC) ≥95%
Sigma-Aldrich
For experimental / research use only.
Chamazulene
analytical standard
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intramuscular-mouse LD50  3000 mg/kg
Rastitel'nye Resursy. Plant Resources. Vol. 3, Pg. 67, 1967.

intravenous-rabbit LDLo  600 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Rastitel'nye Resursy. Plant Resources. Vol. 3, Pg. 67, 1967.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for chamazulene usage levels up to:
 not for fragrance use.
 
Recommendation for chamazulene flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10719
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 7-ethyl-1,4-dimethylazulene
Chemidplus: 0000529055
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References:
 7-ethyl-1,4-dimethylazulene
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 10719
Pubchem (sid): 134975919
Pherobase: View
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C09633
HMDB (The Human Metabolome Database): HMDB36470
FooDB: FDB015363
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 skin conditioning 
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Occurrence (nature, food, other): note
 anise oil
Search Trop  Picture
 artemisia vestita wall. flower oil @ 1.40%
Data  GC  Search Trop  Picture
 artemisia vestita wall. leaf oil @ 1.30%
Data  GC  Search Trop  Picture
 bombycilaena erecta oil greece @ 0.40%
Data  GC  Search Trop  Picture
 callitris intratropica wood oil australia @ 5.60%
Data  GC  Search Trop  Picture
 chamomile
Search  PMC Picture
 chamomile flower oil germany @ 23.35%
Data  GC  Search Trop  Picture
 chamomile garden chamomile plant
Search Trop  Picture
 chamomile sweet false chamomile flower
Search Trop  Picture
 chamomilla recutita (l.) rauschert
PbMd  Search Trop  Picture
 otanthus maritimus (l.) hoffmans oil greece @ 0.80%
Data  GC  Search Trop  Picture
 tanacetum annum l. oil marocco @ 2.80%
Data  GC  Search Trop  Picture
 tansy oil marocco @ 28.00%
Data  GC  Search Trop  Picture
 wormwood oil america @ 0.11%
Data  GC  Search Trop  Picture
 wormwood oil cuba @ 0.26%
Data  GC  Search Trop  Picture
 yarrow oil @ 0.30%
Data  GC  Search Trop  Picture
 yarrow oil hungary @ 12.50%
Data  GC  Search Trop  Picture
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Synonyms:
 azulene, 7-ethyl-1,4-dimethyl-
 camazulene
 dimethulene
1,4-dimethyl-7-(1-methylethyl) azulene
1,4-dimethyl-7-ethyl azulene
1,4-dimethyl-7-ethylazulene
7-ethyl-1,4-dimethyl azulene
7-ethyl-1,4-dimethylazulene
 lindazulene
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Articles:
PubMed: Antinociceptive and anti-edematous activities of the essential oils of two Balkan endemic Laserpitium species.
PubMed: Chemopreventive and antioxidant activity of the chamazulene-rich essential oil obtained from Artemisia arborescens L. growing on the Isle of La Maddalena, Sardinia, Italy.
PubMed: Chemical composition and antifungal activity of Matricaria recutita flower essential oil against medically important dermatophytes and soil-borne pathogens.
PubMed: Pelargonium graveolens L'Her. and Artemisia arborescens L. essential oils: chemical composition, antifungal activity against Rhizoctonia solani and insecticidal activity against Rhysopertha dominica.
PubMed: The organ-specific expression of terpene synthase genes contributes to the terpene hydrocarbon composition of chamomile essential oils.
PubMed: Fast quality assessment of German chamomile (Matricaria chamomilla L.) by headspace solid-phase microextraction: influence of flower development stage.
PubMed: Guaianolides and volatile compounds in chamomile tea.
PubMed: Activity of Matricaria chamomilla essential oil against anisakiasis.
PubMed: Anglo-Saxon pharmacopoeia revisited: a potential treasure in drug discovery.
PubMed: Chemical composition and antibacterial potential of Artemisia arborescens L. essential oil.
PubMed: Variability of the essential oil content and composition of chamomile (Matricaria recutita L.) affected by weather conditions.
PubMed: Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.
PubMed: Content and composition of the essential oil of Chamomilla recutita (L.) Rauschert from some European countries.
PubMed: Chemical composition, antioxidant and antibacterial properties of Achillea collina Becker ex Heimerl s.l. and A. pannonica Scheele essential oils.
PubMed: Genotoxicity of Achillea millefolium essential oil in diploid cells of Aspergillus nidulans.
PubMed: Induction of mitochondrial-dependent apoptosis by an essential oil from Tanacetum gracile.
PubMed: Chemical composition and antibacterial activity of essential oil from Artemisia feddei.
PubMed: Trypanosoma cruzi: activity of essential oils from Achillea millefolium L., Syzygium aromaticum L. and Ocimum basilicum L. on epimastigotes and trypomastigotes.
PubMed: Phytochemical analysis of the essential oil of Achillea millefolium L. from various European Countries.
PubMed: Determination of chamazulene carboxylic acid in serum by high-performance liquid chromatography. Development and validation.
PubMed: Qualitative and quantitative analysis of the active components of the essential oil from Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy.
PubMed: Chamazulene carboxylic acid and matricin: a natural profen and its natural prodrug, identified through similarity to synthetic drug substances.
PubMed: Comparative analysis of the oil and supercritical CO(2) extract of Artemisia arborescens L. and Helichrysum splendidum (Thunb.) Less.
PubMed: A review of the bioactivity and potential health benefits of chamomile tea (Matricaria recutita L.).
PubMed: Inhibitory effects of the essential oil of chamomile (Matricaria recutita L.) and its major constituents on human cytochrome P450 enzymes.
PubMed: Smooth muscle relaxant action of benzyl benzoates and salicylic acid derivatives from Brickellia veronicaefolia on isolated guinea-pig ileum.
PubMed: Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species.
PubMed: Effect of magnesium on essential oil formation of genetically transformed and non-transformed chamomile cultures.
PubMed: [Pharmacognostic research of some species of Achillea. Note 1. Volatile oils analysis].
PubMed: New terpenoids in cultivated and wild chamomile (in vivo and in vitro).
PubMed: Inhibitory effect of chamomile essential oil on the sister chromatid exchanges induced by daunorubicin and methyl methanesulfonate in mouse bone marrow.
PubMed: Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity.
PubMed: Absolute stereochemistry of guaianolides, of matricin and its epimers, of yarrow proazulenes, and of chamazulene carboxylic acid.
PubMed: On the absolute configuration of matricin.
PubMed: Antifungal activity of the essential oil of flowerheads of garland chrysanthemum (Chrysanthemum coronarium) against agricultural pathogens.
PubMed: Production of yarrow (Achillea millefolium L.) in Norway: essential oil content and quality.
PubMed: In vitro study on the transfer of volatile oil components.
PubMed: A study of the production of essential oils in chamomile hairy root cultures.
PubMed: Incorporation of 1-[1-(13)C]Deoxy-D-xylulose in chamomile sesquiterpenes.
PubMed: Investigation of the effect of chamazulene on lipid peroxidation and free radical processes.
PubMed: Effects of some components of the essential oil of chamomile, Chamomilla recutita, on histamine release from rat mast cells.
PubMed: Chamazulene: an antioxidant-type inhibitor of leukotriene B4 formation.
PubMed: Management of oral mucositis during local radiation and systemic chemotherapy: a study of 98 patients.
PubMed: Studies on the Origin of (-)-alpha-Bisabolol and Chamazulene in Chamomile Preparations; Part I. Investigations by Isotope Ratio Mass Spectrometry (IRMS).
PubMed: [Observations and research on an extract of Inula viscosa Ait ].
PubMed: [Pharmacologic studies on chamomile compounds. VI. Studies on the antiphlogistic effect of chamazulene and matricine].
PubMed: Constituents of Essential Oil of Artemisia arborescens.
PubMed: [A chemical study of the essential oil from Artemisia arborescens].
PubMed: [Determination of bisabolol, spiroether and chamazulene in Anthodium Chamomillae].
PubMed: On the quantitative determination of chamazulene and prochamazulenes in essential oils and crude drugs from yarrow (Achillea sp.--Compositae). II.: A new colorimetric method of high sensitivity for determination of chamazulene in the essential oils.
PubMed: [A method for the determination of the chamazulene content of chamomile oil].
PubMed: Quantitative determination of essential oil, total azulenes and chamazulene in German chamomile (Matricaria chamomilla) cultivated in Argentina.
PubMed: [Change in the content of essential oil and chamazulene in German camomile (Matricaria chamomilla L.) during vegetative period].
PubMed: Chamazulene from Artemesia caruthii.
PubMed: [Comparative toxicity of S-guaiazulene, chamazulene and their 3-monosulfone derivatives in white rat].
PubMed: [Studies on the effect of chamazulene on the human skin].
PubMed: [Contribution to the presence and amount of chamazulene in solitary growing plants of the species Achillea millefolium L..].
PubMed: [New possibilities of preparation of chamazulene].
PubMed: Studies on seven-membered ring derivatives. III. Partial synthesis of 1,4-dimethyl-7-ethylazulene (lindazulene).
PubMed: [Antipyretic action of chamazulene].
PubMed: [Further results with chamazulene in the treatment of asthmatic diseases in infancy and childhood].
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