2-methoxycinnamaldehyde: inhibits growth & mycotoxin production in fungi; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 641298 |
| CHEMBL ID | 83159 |
| CHEBI ID | 180713 |
| MeSH ID | M0069035 |
| Synonym |
|---|
| ortho-methoxycinnamaldehyde |
| CHEMBL83159 , |
| 2-methoxy cinnamaldehyde |
| unii-4940g3r6he |
| 4940g3r6he , |
| 2-08-00-00149 (beilstein handbook reference) |
| (2e)-3-(2-methoxyphenyl)prop-2-enal |
| CHEBI:180713 |
| cassiastearoptene |
| (e)-3-(2-methoxyphenyl)prop-2-enal |
| PK04_181244 |
| cinnamaldehyde, o-methoxy- |
| o-methoxycinnamicaldehyde crystals |
| 1504-74-1 |
| 2-methoxycinnamaldehyde |
| o-methoxycinnamic aldehyde |
| 2-propenal, 3-(2-methoxyphenyl)- |
| o-methoxycinnamaldehyde |
| inchi=1/c10h10o2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8h,1h3/b6-4 |
| (2e)-3-(2-methoxyphenyl)acrylaldehyde |
| 2-propenal, 3-(2-methoxyphenyl)-, (2e)- |
| fema no. 3181 |
| 3-o-methoxyphenyl-2-propenal |
| 2'-methoxycinnamaldehyde |
| o-methoxycinnamaldehyde (natural) |
| einecs 216-131-3 |
| nsc 114599 |
| methoxycinnamaldehyde, o- |
| o-methoxyphenyl acrolein, beta- |
| ccris 3196 |
| brn 2436856 |
| 3-(2-methoxyphenyl)-2-propenal |
| beta-(o-methoxyphenyl)acrolein |
| o-methoxycinnamaldehyde, >=96%, fg |
| 2-methoxycinnamaldehyde, predominantly trans, 96% |
| bdbm50240642 |
| (e)-3-(2-methoxy-phenyl)-propenal |
| BRD-K20078988-001-01-1 |
| 3-(2-methoxyphenyl)prop-2-enal |
| AKOS000120956 |
| (e)-3-(2-methoxyphenyl)prop-2-enal;2-methoxycinnamaldehyde, predominantly trans |
| A809049 |
| cas-60125-24-8 |
| tox21_303635 |
| NCGC00256699-01 |
| trans-2-methoxycinnamaldehyde |
| dtxsid4047206 , |
| dtxcid405551 |
| NCGC00260431-01 |
| dtxcid90809802 |
| cas-1504-74-1 |
| dtxsid2025551 , |
| tox21_202885 |
| S9482 |
| o-methoxycinnamaldehyde, (e)- |
| 3gg2b2muhb , |
| unii-3gg2b2muhb |
| 60125-24-8 |
| (e)-3-(2-methoxyphenyl)acrylaldehyde |
| (2e)-3-(2-methoxyphenyl)-2-propenal |
| 2'-methoxycinnamaldehyde (constituent of cinnamomum verum bark) [dsc] |
| trans-o-methoxycinnamaldehyde |
| (e)-2-methoxycinnamaldehyde |
| o-methoxycinnamaldehyde, (2e)- |
| 2-propenal, 3-(2-methoxyphenyl)-, (e)- |
| 2'-methoxycinnamaldehyde (constituent of cinnamomum cassia bark) [dsc] |
| 2-methoxycinnamaldehyde, predominantly trans |
| W-108075 |
| 2-methoxycinnamic aldehyde |
| 3-(2-methoxyphenyl)-2-propenal # |
| ortho methoxy cinnamic aldehyde |
| mfcd00007001 |
| 2'-methoxycinnamaldehyde (constituent of cinnamomum verum bark) |
| 2'-methoxycinnamaldehyde (constituent of cinnamomum cassia bark) |
| 2-methoxycinnamaldehyde, natural, 98%, fg |
| 3-(2-methoxyphenyl)-(2e)-2-propenal |
| beta -(o-methoxyphenyl)acrolein |
| fema 3181 |
| beta-o-methoxyphenyl acrolein |
| o-methoxy-cinnamaldehyde |
| HY-W046353 |
| CS-0201507 |
| AS-15726 |
| AMY3534 |
| O10862 |
| Q27257183 |
| (e)-o-methoxycinnamaldehyde |
| CS-0065992 |
| A869043 |
| 2-methoxycimnamaldehyde |
| EN300-19948 |
| EN300-6729490 |
| Z2573655488 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " The optimal dosage for protection of maize varied from 3 to 8%." | ( Control of Aspergillus flavus in maize with plant essential oils and their components. Carvajal, M; Montes-Belmont, R, 1998) | 0.3 |
| Class | Description |
|---|---|
| cinnamaldehydes | An enal based on a cinnamaldehyde skeleton and its substituted derivatives. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 78.9981 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 31.3476 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 50.5867 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID743042; AID743054; AID743063 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 60.2721 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377; AID1259378 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 42.1669 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 0.3995 | 0.0002 | 14.3764 | 60.0339 | AID720691 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 69.8013 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 69.4984 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 54.9410 | 0.3758 | 27.4851 | 61.6524 | AID743217 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 62.4450 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 55.9264 | 0.0002 | 29.3054 | 16,493.5996 | AID743080 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 48.9662 | 0.0237 | 23.2282 | 63.5986 | AID743222 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 49.8444 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 46.8782 | 0.0016 | 28.0151 | 77.1139 | AID1224843; AID1224895 |
| nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a | Homo sapiens (human) | Potency | 63.3229 | 19.7391 | 45.9784 | 64.9432 | AID1159509 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 56.8110 | 0.0578 | 21.1097 | 61.2679 | AID1159526; AID1159528 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 103.4220 | 0.0391 | 47.5451 | 146.8240 | AID1224845; AID1224896 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 57.1353 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 61.0547 | 0.0420 | 27.3789 | 61.6448 | AID743210; AID743228 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 68.5896 | 0.0006 | 27.2152 | 1,122.0200 | AID743219 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 54.4827 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Polyphenol oxidase 2 | Agaricus bisporus | IC50 (µMol) | 420.0000 | 0.0340 | 3.9871 | 10.0000 | AID467606 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID349481 | Inhibition of bone resorption by mature osteoclast in RANKL-stimulated mouse RAW264.7 cells at 2 uM pretreated for 1 hr measured after 8 days | 2008 | Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20 | Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. |
| AID670364 | Inhibition of xanthine oxidase- mediated uric acid formation after 5 mins by spectrophotometry | 2012 | Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14 | Xanthine oxidase inhibitory activity of constituents of Cinnamomum cassia twigs. |
| AID349479 | Inhibition of multinucleated cell formation in RANKL-stimulated mouse RAW264.7 cells at 0.5 to 2 uM after 3 days by TRAP staining | 2008 | Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20 | Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. |
| AID467606 | Inhibition of mushroom tyrosinase after 10 mins by spectrophotometry | 2009 | Journal of natural products, Jun, Volume: 72, Issue:6 | Tyrosinase-inhibitory constituents from the twigs of Cinnamomum cassia. |
| AID349484 | Inhibition of NF-kappaB transfected in LPS-stimulated mouse RAW264.7 cells | 2008 | Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20 | Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. |
| AID349483 | Inhibition of osteoclastogenesis in RANKL-stimulated mouse RAW264.7 cells at 1 to 2 uM | 2008 | Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20 | Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. |
| AID670363 | Inhibition of xanthine oxidase- mediated uric acid formation at 50 ug/mL after 5 mins by spectrophotometry | 2012 | Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14 | Xanthine oxidase inhibitory activity of constituents of Cinnamomum cassia twigs. |
| AID762798 | Inhibition of Wnt/beta-catenin (unknown origin) signaling pathway expressed in HEK293 cells assessed as inhibition of TCF4 transcriptional activity at 5 to 40 uM after 24 hrs by TOPflash reporter gene assay | 2013 | Journal of natural products, Jul-26, Volume: 76, Issue:7 | Antitumor activity of 2-hydroxycinnamaldehyde for human colon cancer cells through suppression of β-catenin signaling. |
| AID349485 | Inhibition of NF-kappaB activation transfected in RANKL-stimulated mouse RAW264.7 cells at 1 to 2 uM | 2008 | Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20 | Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. |
| AID349478 | Inhibition of NFATc1 expression in RANKL-stimulated mouse RAW264.7 cells after 48 hrs by immunoblotting | 2008 | Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20 | Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. |
| AID349480 | Inhibition of bone resorption by mature osteoclast in RANKL-stimulated mouse RAW264.7 cells pretreated for 1 hr measured after 8 days | 2008 | Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20 | Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. |
| AID349482 | Inhibition of NFATc1 pathway in RANKL-stimulated mouse RAW264.7 cells at 1 to 2 uM | 2008 | Bioorganic & medicinal chemistry, Oct-15, Volume: 16, Issue:20 | Aldehydic components of cinnamon bark extract suppresses RANKL-induced osteoclastogenesis through NFATc1 downregulation. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 3 (9.38) | 18.7374 |
| 1990's | 1 (3.13) | 18.2507 |
| 2000's | 8 (25.00) | 29.6817 |
| 2010's | 13 (40.63) | 24.3611 |
| 2020's | 7 (21.88) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (28.62) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 32 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||