Guaiazulene - 10mM in DMSO , CAS No.489-84-9

CAS: 489-84-9 Cat. No.: G424243 Molecular Weight: 198.31 Beilstein Registry Number: 5(2)473 EC Number: 207-701-2

GRADE & PURITY 10mM in DMSO

Synonyms

Azulene,4-dimethyl- | GUAIAZULENE [WHO-DD] | S-Guaiazulene | 1,4-Dimethyl-7-(1-methylethyl)azulene | 1,4-dimethyl-7-(1-methylethyl)-azulene | UNII-2OZ1K9JKQC | 1,4-Dimethyl-7-(1-methyl)-azulene (azulon) | STK801958 | AZ-8 beris | Azulene, 7-isopropyl-1,4-

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

Azulene, 4-dimethyl- | GUAIAZULENE [WHO-DD] | S-Guaiazulene | 1, 4-Dimethyl-7-(1-methylethyl)azulene | 1, 4-dimethyl-7-(1-methylethyl)-azulene | UNII-2OZ1K9JKQC | 1, 4-Dimethyl-7-(1-methyl)-azulene (azulon) | STK801958 | AZ-8 beris | Azulene, 7-isopropyl-1, 4-

Specifications & Purity

10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CC1=C2C=CC(=C2C=C(C=C1)C(C)C)C
• IUPAC Name: 1,4-dimethyl-7-propan-2-ylazulene
• InChIKey: FWKQNCXZGNBPFD-UHFFFAOYSA-N
• INCHI: 1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3
• Isomeric SMILES: CC1=C2C=CC(=C2C=C(C=C1)C(C)C)C
• WGK Germany: 3
• RTECS: CO4790000
• Molecular Weight: 198.31
• Beilstein: 5(2)473
• Reaxy-Rn: 1365001
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1365001&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Sesquiterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Guaianes
• Alternative Parents: Azulenes Aromatic hydrocarbons Polycyclic hydrocarbons
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Guaiane sesquiterpenoid - Azulene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.
• External Descriptors: Guaiane sesquiterpenoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

U2OS (164939 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

Discover Target: KDM4A

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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GMNN Tbio Geminin (128009 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

Discover Target: CBX1

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

Discover Target: USP1

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Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Flash Point(°F): 230°F
• Flash Point(°C): >110℃
• Boil Point(°C): 153 °C/7 mmHg
• Melt Point(°C): 27-29°C
• Molecular Weight: 198.300 g/mol
• XLogP3: 4.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 198.141 Da
• Monoisotopic Mass: 198.141 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 206.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Chen Pohua, Liu Yang, Zhang Chaochao, Huang Fei, Liu Leifeng, Sun Junliang.  (2022)  Crystalline Sponge Method by Three-Dimensional Electron Diffraction.  Frontiers in Molecular Biosciences,      [PMID:35198600] [10.3389/fmolb.2021.821927]

2. Ye Qin, Zhou Li, Jin Ping, Li Lei, Zheng Shuwen, Huang Zhao, Liu Jiayang, Qin Siyuan, Liu Hao, Zou Bingwen, Xie Ke.  (2021)  Guaiazulene Triggers ROS-Induced Apoptosis and Protective Autophagy in Non-small Cell Lung Cancer.  Frontiers in Pharmacology,      [PMID:33935713] [10.3389/fphar.2021.621181]

3. Yan Yang, Siying Liu, Yan Wang, Qin Yang, Baoan Wang, Yuting Zhang, Zaikang Tong, Junhong Zhang.  (2025)  Antifungal mechanisms of Phoebe bournei wood essential oil against Botryosphaeria dothidea and its application in apples.  POSTHARVEST BIOLOGY AND TECHNOLOGY,      [PMID:] [10.1016/j.postharvbio.2025.113703]