Guaiazulene - ≥99% , CAS No.489-84-9

CAS: 489-84-9 Cat. No.: G137246 Peso molecular: 198.31 Beilstein Registry Number: 5(2)473 Número EC: 207-701-2

GRADE & PURITY ≥99%

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 2-8°C

Shipped In

Wet ice

Descripción general

Application

Guaiazulene can be used as a starting material for the synthesis of: Azulene-based dye molecules such as 3-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanoacrylic acid and 5-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanopenta-2,4-dienoic acid. Stilbazulenyl nitrone, a second-generation azulenyl nitrone which can be used as a chain-breaking antioxidant. Bis-azulenyl based near-infrared fluorescence quencher.

Specifications

Sinónimos

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-

Especificaciones y pureza

≥99%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥99%

Nombres e identificadores

• Pubchem Sid: 504750681
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750681
• Sonrisas canónicas: 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
• Isómeros SMILES: CC1=C2C=CC(=C2C=C(C=C1)C(C)C)C
• WGK Alemania: 3
• RTECS: CO4790000
• Peso molecular: 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
    • Clase Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: 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
• Descripción: 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

Objetivos asociados (humanos)

U2OS (164939 Activities)

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

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

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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)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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

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

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Objetivos asociados (no humanos)

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)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in alcohol, water, 0.1115 mg/L @ 25°C (est).
• Sensibilidad: Light sensitive
• Punto de inflamación (°F): 230°F
• Punto de inflamación (°C): >110℃
• Punto de ebullición (°C): 153 °C/7 mmHg
• Punto de fusión (°C): 27-29°C
• Peso molecular: 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

Referencias

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]