2-hydroxycinnamaldehyde
cinnamaldehyde, 2-hydroxy-
Identification
| Name | 2-hydroxycinnamaldehyde |
| IUPAC | (E)-3-(2-hydroxyphenyl)prop-2-enal |
| CAS Number | 3541-42-2 |
| FDA UNII | Search |
| Molecular Formula | C9 H8 O2 |
| Molecular Weight | 148.16116000 |
| MDL Number | MFCD01736614 |
| Nikkaji Number | J533.508F |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 311.00 to 312.00 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.000310 mmHg @ 25.00 °C. (est) |
| Flash Point | 269.00 °F. TCC ( 131.80 °C. ) (est) |
| logP (o/w) | 1.674 (est) |
| Soluble in | alcohol |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | unreported-rat LD50 750 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for 2-hydroxycinnamaldehyde usage levels up to | not for fragrance use. |
| Recommendation for 2-hydroxycinnamaldehyde flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
cinnamaldehyde, 2-hydroxy-
cinnamaldehyde, o-hydroxy-
(E)-3-(2-
hydroxy-phenyl)-propenal
2'-
hydroxycinnamaldehyde
o-
hydroxycinnamaldehyde
ortho-
hydroxycinnamaldehyde
2-
hydroxycinnamic aldehyde
(E)-3-(2-
hydroxyphenyl) prop-2-enal
3-(2-
hydroxyphenyl)-2-propenal
(2E)-3-(2-
hydroxyphenyl)acrylaldehyde
(2E)-3-(2-
hydroxyphenyl)prop-2-enal
(E)-3-(2-
hydroxyphenyl)prop-2-enal
2-
propenal, 3-(2-hydroxyphenyl)-
2-
propenal, 3-(2-hydroxyphenyl)-, (2E)-
PubMed:
A new coumarin and cytotoxic activities of constituents from Cinnamomum cassia.
PubMed:
LRP1-dependent pepsin clearance induced by 2'-hydroxycinnamaldehyde attenuates breast cancer cell invasion.
PubMed:
[Chemical constituents from Elephantopus tomentosus].
PubMed:
Antitumor activity of 2-hydroxycinnamaldehyde for human colon cancer cells through suppression of β-catenin signaling.
PubMed:
2-Hydroxycinnamaldehyde inhibits the epithelial-mesenchymal transition in breast cancer cells.
PubMed:
Induction of tumor cell death through targeting tubulin and evoking dysregulation of cell cycle regulatory proteins by multifunctional cinnamaldehydes.
PubMed:
2'-Benzoyloxycinnamaldehyde inhibits nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 cells via regulation of AP-1 pathway.
PubMed:
2-Hydroxycurcuminoid induces apoptosis of human tumor cells through the reactive oxygen species-mitochondria pathway.
PubMed:
Differential antiproliferation effect of 2'-benzoyloxycinnamaldehyde in K-ras-transformed cells via downregulation of thiol antioxidants.
PubMed:
2'-Hydroxycinnamaldehyde targets low-density lipoprotein receptor-related protein-1 to inhibit lipopolysaccharide-induced microglial activation.
PubMed:
Platelet anti-aggregation activities of compounds from Cinnamomum cassia.
PubMed:
2'-Hydroxycinnamaldehyde shows antitumor activity against oral cancer in vitro and in vivo in a rat tumor model.
PubMed:
Transport and metabolism of the antitumour drug candidate 2'-benzoyloxycinnamaldehyde in Caco-2 cells.
PubMed:
Cinnamaldehydes inhibit thioredoxin reductase and induce Nrf2: potential candidates for cancer therapy and chemoprevention.
PubMed:
Structure-activity analysis of 2'-modified cinnamaldehyde analogues as potential anticancer agents.
PubMed:
Plasma pharmacokinetics and metabolism of the antitumour drug candidate 2'-benzoyloxycinnamaldehyde in rats.
PubMed:
Synthesis and biological evaluation of cinnamyl compounds as potent antitumor agents.
PubMed:
Apoptosis induction of 2'-hydroxycinnamaldehyde as a proteasome inhibitor is associated with ER stress and mitochondrial perturbation in cancer cells.
PubMed:
2-hydroxycinnamaldehyde inhibits SW620 colon cancer cell growth through AP-1 inactivation.
PubMed:
Delayed occurrence of H-ras12V-induced hepatocellular carcinoma with long-term treatment with cinnamaldehydes.
PubMed:
Synthesis and biological evaluation of dimeric cinnamaldehydes as potent antitumor agents.
PubMed:
Induction of apoptotic cell death by 2'-hydroxycinnamaldehyde is involved with ERK-dependent inactivation of NF-kappaB in TNF-alpha-treated SW620 colon cancer cells.
PubMed:
Inhibitory effect of 2'-hydroxycinnamaldehyde on nitric oxide production through inhibition of NF-kappa B activation in RAW 264.7 cells.
PubMed:
Physicochemical properties of 2'-benzoyloxycinnamaldehyde.
PubMed:
2'-benzoyloxycinnamaldehyde induces apoptosis in human carcinoma via reactive oxygen species.
PubMed:
Antitumor effect of the cinnamaldehyde derivative CB403 through the arrest of cell cycle progression in the G2/M phase.
PubMed:
Constituents of the essential oil of the Cinnamomum cassia stem bark and the biological properties.
PubMed:
Inhibition of human tumor growth by 2'-hydroxy- and 2'-benzoyloxycinnamaldehydes.
PubMed:
Synthesis and in vitro cytotoxicity of cinnamaldehydes to human solid tumor cells.
PubMed:
Cinnamaldehyde inhibits lymphocyte proliferation and modulates T-cell differentiation.
PubMed:
2'-Hydroxycinnamaldehyde from stem bark of Cinnamomum cassia.