Curcumol - Moligand™, ≥98% , CAS No.4871-97-0

CAS: 4871-97-0 Cat. No.: C1209423 Peso molecular: 236.35

GRADE & PURITY Moligand™, ≥98%

Synonyms

( -)-Curcumol | analytical standard | C3439 | AC-34186 | Q-100546 | SCHEMBL22404924 | NCGC00346607-02 | (1S,2S,5S,8R,9S)-2-methyl-6-methylidene-9-propan-2-yl-11-oxatricyclo[6.2.1.01,5]undecan-8-ol | CCG-266844 | ( -)-Curcumol | Q27271386

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Specifications

Sinónimos

( -)-Curcumol | analytical standard | C3439 | AC-34186 | Q-100546 | SCHEMBL22404924 | NCGC00346607-02 | (1S, 2S, 5S, 8R, 9S)-2-methyl-6-methylidene-9-propan-2-yl-11-oxatricyclo[6.2.1.01, 5]undecan-8-ol | CCG-266844 | ( -)-Curcumol | Q27271386

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Biochemical Mechanism: Anti-inflammatory and antiproliferative agent. Inhibits LPS-induced NO production by inhibiting iNOS mRNA expression. Inhibits TNF-α, IL-1β, and IL-6 production. Induces p53 activation and G1 cell cycle arrest. Promotes angiogenesis

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C, Protected from light

Enviado en

Wet ice

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

Grado

Moligand™

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CC1CCC2C13CC(C(O3)(CC2=C)O)C(C)C
• IUPAC Name: (1S,2S,5S,8R,9S)-2-methyl-6-methylidene-9-propan-2-yl-11-oxatricyclo[6.2.1.01,5]undecan-8-ol
• InChIKey: QRMPRVXWPCLVNI-YYFQZIEXSA-N
• INCHI: 1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3/t11-,12-,13-,14-,15+/m0/s1
• Isómeros SMILES: C[C@H]1CC[C@@H]2[C@]13C[C@H]([C@](O3)(CC2=C)O)C(C)C
• Peso molecular: 236.35
• Reaxy-Rn: 2111893
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2111893&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: Oxanes Tetrahydrofurans Hemiacetals Cyclic alcohols and derivatives Oxacyclic compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Guaiane sesquiterpenoid - Oxane - Tetrahydrofuran - Cyclic alcohol - Hemiacetal - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteropolycyclic 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: Not available

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

Propiedades químicas y físicas

• Sensibilidad: Light sensitive
• Peso molecular: 236.350 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 236.178 Da
• Monoisotopic Mass: 236.178 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 362.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• 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. Shuai-Nan Zhang, Qi Liu, Xu-Zhao Li, Wu-De Yang, Ying Zhou.  (2023)  Liver protein and metabolite biolabels reveal hepatoprotective effects and active compounds of Eucommiae folium: Exploration of new application of herb based on multi-omics and bioinformatics.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:38008044] [10.1016/j.jpba.2023.115870]

2. Xuelin Duan, Tiejian Zhao, Jiaru Wang, Jiahui Wang, Yang Zheng.  (2023)  Curcumol targets glutaminase 1 to regulate glutamine metabolism and induce senescence of hepatic stellate cells.  European Journal of Integrative Medicine,      [PMID:] [10.1016/j.eujim.2023.102278]

3. Yang Zheng, Tiejian Zhao, Jiaru Wang, Ruizhu Jiang, Jinbiao Huang, Weimin Li, Jiahui Wang.  (2022)  Curcumol alleviates liver fibrosis through inducing autophagy and ferroptosis in hepatic stellate cells.  FASEB JOURNAL,  36  (12): (e22665).  [PMID:36398583] [10.1096/fj.202200933RR]

4. Yang Zheng, Jiahui Wang, Jiaru Wang, Ruizhu Jiang, Tiejian Zhao.  (2022)  Gut microbiota combined with metabolomics reveal the mechanism of curcumol on liver fibrosis in mice.  BIOMEDICINE & PHARMACOTHERAPY,      [PMID:35653891] [10.1016/j.biopha.2022.113204]

5. Yang Zheng, Jiaru Wang, Tiejian Zhao, Lei Wang, Jiahui Wang.  (2021)  Modulation of the VEGF/AKT/eNOS signaling pathway to regulate liver angiogenesis to explore the anti-hepatic fibrosis mechanism of curcumol.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:34358654] [10.1016/j.jep.2021.114480]

6. Yang Zheng, Jiahui Wang, Jiaru Wang, Haiyuan Xie, Tiejian Zhao.  (2020)  Effect of Curcumol on the Fenestrae of Liver Sinusoidal Endothelial Cells Based on NF-κB Signaling Pathway.  Evidence-based Complementary and Alternative Medicine,      [PMID:32595742] [10.1155/2020/8590638]

7. Kong L.M., Xu S.Y., Hu H.H., Zhou H., Jiang H.D., Yu L.S., Zeng S..  (2014)  Identification of CYP2C19 inhibitors from phytochemicals using the recombinant human enzyme model.  PHARMAZIE,  69  (5): (362-366).  [PMID:] [10.1691/ph.2014.3194]

8. Jingjing Yang, Hai Zhu, Wenhao Liang, Xingzeng Zhao, Min Yin, Xu Feng, Bi Wang.  (2024)  Fungicidal activity of curcumol against Phytophthora capsici via inhibiting phosphatidylcholine biosynthesis and its systemic translocation in plants.  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:39672648] [10.1016/j.pestbp.2024.106214]

9. Yao Wang, Junhua Qiu, Chengwei Wang, Ruiyu Yang, Fuyou Guo, Tian Li, Shili Li, Lei Yang, Wei Ding.  (2026)  Sustainable Strategy of Natural trans-Anethole in Controlling Bacterial Wilt: Virulence Suppression and Beneficial Microbiome Enrichment.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41568748] [10.1021/acs.jafc.5c13627]