Chamazulene | CAS#529-05-5 | Inhibitor of Leukotriene B4 Formation

MedKoo Cat#: 584118 | Name: Chamazulene

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Chamazulene

CAS#529-05-5

Theoretical Analysis

MedKoo Cat#: 584118

Name: Chamazulene

CAS#: 529-05-5

Chemical Formula: C14H16

Exact Mass: 184.1252

Molecular Weight: 184.28

Elemental Analysis: C, 91.25; H, 8.75

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 425.00	2 Weeks
5mg	USD 1,450.00	2 Weeks

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Related CAS #

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Synonym

Chamazulene; Chamazulen; Dimethulene; BA 2784; BA-2784; BA2784;

IUPAC/Chemical Name

7-Ethyl-1,4-dimethylazulene

InChi Key

GXGJIOMUZAGVEH-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3

SMILES Code

CC1=C2C=CC(C)=C2C=C(CC)C=C1

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 184.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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.