2D Structure

3D Structure

Cinnamic Acid


Properties
PID PID00011
Mol. Weight 148.161 g/mol
LogP 2.13
Water solubility 0.546 mg/m
Hydrogen Bond Donor 1
Hydrogen Bond Acceptor 2
Rotatable Bonds 2
XLogP3 2.1

Cinnamic Acid

Identifiers
Formula C9H8O2
PubChem CID 444539
FEMA 2288
Flavor Profile None
Smiles O=C(O)/C=C/c1ccccc1
InChl Key WBYWAXJHAXSJNI-VOTSOKGWSA-N
InChl InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
CAS Registry Number 140-10-3, 621-82-9
IUPAC Systematic Name (E)-3-phenylprop-2-enoic acid

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
Cassiabarktree TwigGui Zhi (桂枝)Cinnamomi RamulusWarm, Pungent, SweetLung, Bladder, HeartView Graph
Oriental Sweetgum ResinSu He Xiang (苏合香)StyraxWarm, PungentLung, Spleen, StomachView Graph
Styrax benzoinAn Xi Xiang(安息香)Sumatra Snowbell Equivalent plant: Styrax tonkinenMild,Pungent,BitterSpleen,HeartView Graph
Rhizoma TyphoniiBai Fu Zi(白附子)rhizome of Giant TyphoniumWarm,Pungent,SweetSpleen,Liver,HeartView Graph
Barbed SkullcapBan Zhi Lian(半枝莲)Scutellariae Barbatae HerbaCold, Bitter, PungentBladder, Spleen, Liver,StomachView Graph
Fineleaf SchizonepetaJing Jie (荆芥)Schizonepetae HerbaMinor Warm, PungentLung, LiverView Graph
Chinese Ephedra Equivalent plant: Ephedra equisetiMa Huang (麻黄)Ephedrae HerbaWarm, Pungent, Slightly BitterLung, BladderView Graph
Common GoldenrodYi Zhi Huang Hua(一枝黄花)Solidaginis HerbaCool, Bitter, PungentLiver, LungView Graph
Lesser GalangalGao Liang Jiang (高良姜)Alpiniae Officinarum RhizomaHot,PungentLarge Intestine, StomachView Graph
Cassiabarktree TwigGui Zhi (桂枝)Cinnamomi RamulusWarm, Pungent, SweetLung, Bladder, HeartView Graph
SafflowerHong Hua (红花)Carthami FlosWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Fresh Common GingerSheng Jiang(生姜 )Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
CassiabarktreeRou Gui (肉桂)Cinnamomi CortexHot, Sweet, PungentLiver, Heart, Spleen, KidneyView Graph
Round Cardamon FruitDou Kou (豆蔻)Amomi Fructus RotundusWarm, Pungent,Spleen, Lung, StomachView Graph

Pharmacological action

Cinnamic Acid occurs naturally in a number of plants, Cinnamic acid has a honey-like odor; it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. Modern pharmacological studies have demonstrated thatAntimicrobial and demelanizing activity Cinnamic multiple functions, includingAcid antioxidants, antidiabetic active, inhibition of detritus feeding,hNK2 receptor antagonists, anti-hepatitis B virus, inhibit HIV/SARS-CoV S pseudovirus, anti-poliovirus type 1 (PV1) activity,Skin irritation, Skin sensitization. Meanwhile, cinnamic acid has been widely applied as a food additive with good safety.



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

1 Vogt T. Phenylpropanoid biosynthesis[J]. Molecular plant, 2010, 3(1): 2-20.

2 Heleno S A, Ferreira I C F R, Esteves A P, et al. Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters[J]. Food and chemical toxicology, 2013, 58: 95-100.

3 Li Y, Dai F, Jin X L, et al. An effective strategy to develop active cinnamic acid-directed antioxidants based on elongating the conjugated chains[J]. Food chemistry, 2014, 158: 41-47.

4 Kasetti R B, Nabi S A, Swapna S, et al. Cinnamic acid as one of the antidiabetic active principle (s) from the seeds of Syzygium alternifolium[J]. Food and chemical toxicology, 2012, 50(5): 1425-1431.

5 Valiela I, Koumjian L, Swain T, et al. Cinnamic acid inhibition of detritus feeding[J]. Nature, 1979, 280(5717): 55.

6 Porcelloni M, DAndrea P, Altamura M, et al. Cinnamic acids and mono-substituted benzoic acids as useful capping groups for the preparation of hNK 2 receptor antagonists[J]. Bioorganic & medicinal chemistry letters, 2008, 18(16): 4705-4707.

7 Wang L J, Geng C A, Ma Y B, et al. Design, synthesis, and molecular hybrids of caudatin and cinnamic acids as novel anti-hepatitis B virus agents[J]. European journal of medicinal chemistry, 2012, 54: 352-365.

8 Zhuang M, Jiang H, Suzuki Y, et al. Procyanidins and butanol extract of Cinnamomi Cortex inhibit SARS-CoV infection[J]. Antiviral research, 2009, 82(1): 73-81.

9 Galabov A S, Nikolaeva L, Todorova D, et al. Antiviral activity of cholesteryl esters of cinnamic acid derivatives[J]. Zeitschrift fr Naturforschung C, 1998, 53(9-10): 883-887.

10 Letizia C S, Cocchiara J, Lapczynski A, et al. Fragrance material review on cinnamic acid[J]. Food and Chemical Toxicology, 2005, 43(6): 925-943.