2D Structure

3D Structure

Anethole


Properties
PID PID00203
Mol. Weight 148.205 g/mol
LogP 2.94
Water solubility 0.1110 g/l
Hydrogen Bond Donor 0
Hydrogen Bond Acceptor 1
Rotatable Bonds 2
XLogP3 3.3

Anethole

Identifiers
Formula C10H12O
PubChem CID 637563
FEMA 2086
Flavor Profile Anise, Anise Oil Odor, Sweet Taste,
Smiles CC=CC1=CC=C(C=C1)OC
InChl Key RUVINXPYWBROJD-ONEGZZNKSA-N
InChl InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
CAS Registry Number 104-46-1, 50770-19-9, 4180-23-8
IUPAC Systematic Name 1-methoxy-4-[(E)-prop-1-enyl]benzene

Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets


Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)


Related Pungent TCM

English Name Pinyin Name (Chinese Name) Latin Name Properties in TCM merdians View Graph
Chinese Star AniseBa Jiao Hui Xiang (八角茴香)Anisi Stellati FructusWarm, PungentLung, Spleen, StomachView Graph
Croton tigliumBa Dou(巴豆)Pu rging CrotonPu rging CrotonHot,PungentView Graph
Dahurian AngelicaBai Zhi(白芷)Angelicae Dahuricae RadixAngelicae Dahuricae RadixWarm, PungentView Graph
Ternate PinelliaBan Xia(半夏)Pinellia ternataPinellia ternataWarm,PungentView Graph
Long PepperBi Ba (荜茇)Piperis Longi FructusPiperis Longi FructusHot,PungentView Graph
Cablin PotchouliGuang Huo Xiang (广藿香)Pogostemonis HerbaPogostemonis HerbaMinor Warm,PungentView Graph
Cassiabarktree TwigGui Zhi (桂枝)Cinnamomi RamulusCinnamomi RamulusWarm, Pungent, SweetView Graph
Black PepperHu Jiao (胡椒)Piperis FructusPiperis FructusHot,PungentView Graph
Bunge Pricklyash Equivalent plant: Zanthoxylum schHua Jiao (花椒)Zanthoxyli PericarpiumZanthoxyli PericarpiumWarm,PungentView Graph
Exocarpium Citri grandisHua Ju Hong(化橘红)Pummelo PeelPummelo PeelMild,BitterView Graph
Common Turmeric Equivalent plant: Curcuma aromatiJiang Huang (姜黄)Curcumae Longae RhizomaCurcumae Longae RhizomaWarm, Pungent, BitterView Graph
Common Aucklandia (Costustoot)Mu Xiang(木香)Aucklandiae RadixAucklandiae RadixWarm, Bitter, PungentView Graph
Fortune Eupatorium Equivalent plant: Eupatorium fPei Lan(佩兰)Eupatorii HerbaEupatorii HerbaNeural, PungentView Graph
CassiabarktreeRou Gui (肉桂)Cinnamomi CortexCinnamomi CortexHot, Sweet, PungentView Graph
Common Japanese Clubmoss Equivalent plant: LycopodShen Jin Cao(伸筋草)Lycopodii HerbaLycopodii HerbaWarm, Bitter, PungentView Graph
Bugbane Equivalent plant: Cimicifuga dahurica, CiSheng Ma(升麻)Cimicifugae RhizomaCimicifugae RhizomaCold, Sweet, PungentView Graph
Fennel FruitXiao Hui Xiang (小茴香)Foeniculi FructusFoeniculi FructusWarm, PungentView Graph
Aster tataricusZi Wan(紫菀)Tatarion AsterTatarion AsterWarm,Pungent,Sweet,BitterView Graph

Pharmacological action

Anethole restores gastric emptying independently of D2, 5-HT3 and 5-HT4 receptors. It is the main fragrance and bioactive compound. It is safety. It is widely used as flavor agent in food industry and other industries, in cosmetics, perfumery, and pharmaceuticals. It has anti-inflammatory, anticarcinogenic and chemopreventive, antidiabetic, immunomodulatory, neuroprotective, anti-metastatic or antithrombotic effects. It also has an important antinociceptive activity, antifungal activities, oestrogenic activity, hepatoprotective activity, antidiabetic activity, acaricidal activity, antihirustism activity and gastroprotector activity. It can modulate several cell signaling pathways, mainly NF-kB and TNF-a signaling, and various ion channels mediate. The combinatorial use of anethole with cyclophosphamide, a classic anticancer drug, exhibits more tumoricidal activity. Anethole can accelerate wound closure of injured tissue, enhances the number of fibroblasts and collagen fibers. It has a positive effect of anethole on meiosis resumption of oocytes from caprine secondary follicles grown in vitro. It can prevent H2O2-induced collagen metabolism alterations and apoptosis in human skin fibroblasts. Different doses of anethole suppressed paw swelling and the number of serum and synovial leukocytes. Anethole induce an initial fall in blood pressure followed by a pressor response. It can reduce the intensity of oxytocin and PGE2 induced contractions significantly. Fennel essential oil also reduced the frequency of contractions induced by PGE2 but not with oxytocin. It induces contraction of rat vascular smooth muscle via the direct or indirect opening of VDCCs at micromolar concentrations. It has an important role in regulating activities of mTOR/PPAR and ROS control in adipogenic differentiation of hMSCs. It has an effect on transcriptional programming via mTOR and AMPK by reducing excessive ROS.



Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.

References

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45. https://en.wikipedia.org/wiki/Terpinene