Chamazulene

• CAT Number: I024522
• CAS Number: 529-05-5
• Molecular Formula: C14H16
• Molecular Weight: 184.28
• Purity: 98%
• Synonyms: Chamazulene; Dimethulene; BA 2784; BA-2784; BA2784
• Target: Leukotriene Receptor
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 7-Ethyl-1,4-dimethylazulene
• InChI: InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3
• InChIKey: GXGJIOMUZAGVEH-UHFFFAOYSA-N
• SMILES: CC1=C2C=CC(C)=C2C=C(CC)C=C1

Chamazulene is an anti-inflammatory agent as well as antioxidant-type inhibitor of leukotriene B4 formation and may contribute to the anti-inflammatory activity of chamomile extracts with additional antioxidative effects.

Reference

1: Abdelhameed RM, Abdel-Gawad H, Taha M, Hegazi B. Separation of bioactive chamazulene from chamomile extract using metal-organic framework. J Pharm Biomed Anal. 2017 Nov 30;146:126-134. doi: 10.1016/j.jpba.2017.08.020. Epub 2017 Aug 26. PubMed PMID: 28869815.
2: Ghasemi M, Babaeian Jelodar N, Modarresi M, Bagheri N, Jamali A. Increase of Chamazulene and α-Bisabolol Contents of the Essential Oil of German Chamomile (Matricaria chamomilla L.) Using Salicylic Acid Treatments under Normal and Heat Stress Conditions. Foods. 2016 Aug 27;5(3). pii: E56. doi: 10.3390/foods5030056. PubMed PMID: 28231151; PubMed Central PMCID: PMC5302395.
3: Flemming M, Kraus B, Rascle A, Jürgenliemk G, Fuchs S, Fürst R, Heilmann J. Revisited anti-inflammatory activity of matricine in vitro: Comparison with chamazulene. Fitoterapia. 2015 Oct;106:122-8. doi: 10.1016/j.fitote.2015.08.010. Epub 2015 Aug 21. PubMed PMID: 26304764.
4: Capuzzo A, Occhipinti A, Maffei ME. Antioxidant and radical scavenging activities of chamazulene. Nat Prod Res. 2014;28(24):2321-3. doi: 10.1080/14786419.2014.931393. Epub 2014 Jul 1. PubMed PMID: 24980540.
5: Ornano L, Venditti A, Ballero M, Sanna C, Quassinti L, Bramucci M, Lupidi G, Papa F, Vittori S, Maggi F, Bianco A. Chemopreventive and antioxidant activity of the chamazulene-rich essential oil obtained from Artemisia arborescens L. growing on the Isle of La Maddalena, Sardinia, Italy. Chem Biodivers. 2013 Aug;10(8):1464-74. doi: 10.1002/cbdv.201200435. PubMed PMID: 23939794.
6: Ramadan M, Goeters S, Watzer B, Krause E, Lohmann K, Bauer R, Hempel B, Imming P. Chamazulene carboxylic acid and matricin: a natural profen and its natural prodrug, identified through similarity to synthetic drug substances. J Nat Prod. 2006 Jul;69(7):1041-5. PubMed PMID: 16872141.
7: Safayhi H, Sabieraj J, Sailer ER, Ammon HP. Chamazulene: an antioxidant-type inhibitor of leukotriene B4 formation. Planta Med. 1994 Oct;60(5):410-3. PubMed PMID: 7997466.
8: Rekka EA, Kourounakis AP, Kourounakis PN. Investigation of the effect of chamazulene on lipid peroxidation and free radical processes. Res Commun Mol Pathol Pharmacol. 1996 Jun;92(3):361-4. PubMed PMID: 8827832.
9: Carle R, Fleischhauer I, Beyer J, Reinhard E. Studies on the Origin of (-)-alpha-Bisabolol and Chamazulene in Chamomile Preparations; Part I. Investigations by Isotope Ratio Mass Spectrometry (IRMS). Planta Med. 1990 Oct;56(5):456-60. PubMed PMID: 17221447.
10: Jakovlev V, Isaac O, Flaskamp E. [Pharmacologic studies on chamomile compounds. VI. Studies on the antiphlogistic effect of chamazulene and matricine]. Planta Med. 1983 Oct;49(2):67-73. German. PubMed PMID: 6657784.
11: Debska W, Bartkowiakowa T. [Determination of bisabolol, spiroether and chamazulene in Anthodium Chamomillae]. Acta Pol Pharm. 1978;35(6):699-700. Polish. PubMed PMID: 742402.
12: Verzár-Petri G, Cuong BN. 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. Acta Pharm Hung. 1977 May;47(3):134-41. PubMed PMID: 878884.
13: Gizella VP, Gabriella M. [A method for the determination of the chamazulene content of chamomile oil]. Acta Pharm Hung. 1976 Nov;46(5-6):282-8. Hungarian. PubMed PMID: 1020654.
14: Padula LZ, Rondina RV, Coussio JD. Quantitative determination of essential oil, total azulenes and chamazulene in German chamomile (Matricaria chamomilla) cultivated in Argentina. Planta Med. 1976 Nov;30(3):273-80. PubMed PMID: 1005530.
15: Kiseleva EIa, Rybalko KS, Loshkarev PM, Glazova MV. [Change in the content of essential oil and chamazulene in German camomile (Matricaria chamomilla L.) during vegetative period]. Farmatsiia. 1969 Jul-Aug;18(4):34-9. Russian. PubMed PMID: 5379649.
16: CAUJOLLE F, MEYNIER D, HUYNH NA. [Comparative toxicity of S-guaiazulene, chamazulene and their 3-monosulfone derivatives in white rat]. C R Hebd Seances Acad Sci. 1957 Nov 18;245(21):1846-8. French. PubMed PMID: 13489933.
17: HUBACKOVA L. [Studies on the effect of chamazulene on the human skin]. Cesk Dermatol. 1956 Dec;31(6):343-6. Czech. PubMed PMID: 13404639.
18: KUCERA M, MACKEOVA E. [Contribution to the presence and amount of chamazulene in solitary growing plants of the species Achillea millefolium L..]. Cesk Farm. 1955 Mar;4(2):78-80. Czech. PubMed PMID: 14379238.
19: HEROUT V. [New possibilities of preparation of chamazulene]. Cesk Farm. 1954 Dec;3(10):333-6. Czech. PubMed PMID: 14364590.
20: BLAZSO S. [Further results with chamazulene in the treatment of asthmatic diseases in infancy and childhood]. Schweiz Med Wochenschr. 1951 Feb 3;81(5):110-1. Undetermined Language. PubMed PMID: 14845650.