Caffeic acid ethyl ester
ETHYL CAFFEATE
CAS: 102-37-4
Molecular Formula: C11H12O4
Caffeic acid ethyl ester - Names and Identifiers
| Name | ETHYL CAFFEATE |
| Synonyms | ETHYL CAFFEATE Caffeoyl ethyl ester Caffeic acid ethyl ester CAFFEIC ACID ETHYLESTER(RG) 3,4-Dihydroxycinnamic acid ethyl ester 3,4-Dihydroxybenzeneacrylic acid ethyl ester Ethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate 3-(3,4-Dihydroxyphenyl)acrylic acid ethyl ester ethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate 3-(3,4-Dihydroxyphenyl)propenoic acid ethyl ester 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester |
| CAS | 102-37-4 |
| EINECS | 000-000-0 |
| InChI | InChI=1/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3/b6-4+ |
Caffeic acid ethyl ester - Physico-chemical Properties
| Molecular Formula | C11H12O4 |
| Molar Mass | 208.21 |
| Density | 1.271±0.06 g/cm3(Predicted) |
| Melting Point | 149.5 °C |
| Boling Point | 377.0±32.0 °C(Predicted) |
| Flash Point | 148.4°C |
| Solubility | DMSO : 250 mg/mL (1200.71 mM; Need ultrasonic) |
| Vapor Presure | 3.22E-06mmHg at 25°C |
| Appearance | Powder |
| pKa | 8.71±0.18(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.612 |
| MDL | MFCD00045754 |
| In vitro study | Ethyl Caffeate markedly suppresses the lipopolysaccharide (LPS)-induced nitric oxide (NO) production with IC 50 of 5.5 μg/ml. |
Caffeic acid ethyl ester - Reference
| Reference Show more | 1. [IF=4.411] Li Jia et al."Systematic Profiling of the Multicomponents and Authentication of Erzhi Pill by UHPLC/Q-Orbitrap-MS Oriented Rapid Polarity-Switching Data-Dependent Acquisition and Selective Monitoring of the Chemical Markers Deduced from Fingerprint Analys 2. [IF=3.645] Lewen Xiong et al."Study on phenolic acids of Lonicerae japonicae Flos based on ultrahigh performance liquid chromatography-tandem mass spectrometry combined with multivariate statistical analysis."JOURNAL OF SEPARATION SCIENCE 3. [IF=3.645] Lewen Xiong et al."Study on phenolic acids of Lonicerae japonicae Flos based on ultrahigh performance liquid chromatography-tandem mass spectrometry combined with multivariate statistical analysis."JOURNAL OF SEPARATION SCIENCE |
Caffeic acid ethyl ester - Reference Information
| overview | caffeic acid ethyl ester is an important active ingredient of morning glory, which has anti-inflammatory effect and potential for treating autoimmune diseases. picture: morning glory |
| extraction process of caffeic acid ethyl ester from morning glory | method: organic solvent extraction method was used, and the extraction rate of caffeic acid and caffeic acid ethyl ester was used as index, and L16(44) orthogonal test was used to optimize the extraction process. Results: The optimum extraction conditions were as follows: ethanol with 95% volume fraction was used as extractant, extracted at 70 ℃ for 4 h, and the ratio of solid to liquid was 1 ∶ 20(g/ml). Conclusion: The method is simple to operate, with high extraction rate of caffeic acid and ethyl caffeic acid and good stability. |
| pharmacological mechanism | the molecular mechanism of caffeic acid ethyl ester inhibiting lymphocyte activation lays the foundation for the development of caffeic acid ethyl ester into a new drug for the treatment of autoimmune diseases. Methods CCK-8 and ELISA methods were used to determine the levels of caffeic acid ethyl ester on mitogen-induced splenic lymphocyte proliferation and cytokine (IL-2, IFN-and IL-6) production. To establish ovalbumin (induced antigen-specific immune response, and to detect the cell activation and cytokine (IL-2, IFN-) secretion of caffeic acid ethyl ester in vivo; real-time fluorescence quantitative detection of cytokines (IL-2, IFN-) and related transcription factors (T-BET and SAT1) expression; Determination and signal-mediated signaling pathway (and phosphorylation level. Results Caffeic acid ethyl ester significantly inhibited the proliferation and cytokine production of induced spleen lymphocytes in normal mice. In vivo oral caffeic acid ethyl ester significantly inhibited the induction of antigen-specific cell proliferation and cytokine and production levels. It can significantly inhibit the expression of IL-2, IFN-, T-BET and SAT1m-RNA at the transcription level. Caffeic acid ethyl ester can effectively inhibit and signal-mediated MAPK signaling pathways (TCR/CD3 and CD28), of which P38 is the most obvious. Conclusion: caffeic acid ethyl ester, an effective component of gilanthus, may interfere with IL-2, IFN-, T-BET and SAT1 signaling pathways, down-regulate transcription factors and expression of BET and SAT1 signals, inhibit production and cell activation by inhibiting phosphorylation of MAPK signaling pathways (P38 and ERKI/2). |
| references | [1] Gao Zhongliang, Zhang Liying, Li Mengqing, et al. Study on Extraction of Caffeic Acid and Ethyl Caffeic Acid from Morning Glory [J]. Anhui Agricultural Sciences, 2009, 37(7):3049-3050. [2] Wan Chunping, Qi Yan, Zheng Xi, based on MAPK signaling pathway, study on the molecular mechanism of caffeic acid ethyl ester, a component of gileae, inhibiting T cell activation [C]// National Academic Conference on Rheumatism of Integrated Traditional Chinese and Western Medicine. 2014. |
| biological activity | Ethyl Caffeate is a natural phenolic compound isolated from Bidens pilosa. Ethyl Caffeate inhibits NF-κB activation and its downstream inflammatory mediators, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) and prostaglandin E2 (PGE2) in vitro or in mouse skin. |
| use | for content determination/identification/pharmacological experiments, etc. |
Last Update：2024-04-09 15:16:46
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View History
Caffeic acid ethyl ester
氯甲醚三苯基膦盐
硬脂基二乙醇胺
Propargyl bromide
H-ILE-ILE-ILE-OH
disodium 6-amino-4-hydroxy-5-[(4-nitro-2-sulphonatophenyl)azo]naphthalene-2-sulphonate
5-HYDROXY-2-NITROBENZOIC ACID
L-Homocystine
Dimethylaminoacethyhydrazide hydrochloride
N-(二硫代羧基)肌氨酸
氯甲醚三苯基膦盐
硬脂基二乙醇胺
Propargyl bromide
H-ILE-ILE-ILE-OH
disodium 6-amino-4-hydroxy-5-[(4-nitro-2-sulphonatophenyl)azo]naphthalene-2-sulphonate
5-HYDROXY-2-NITROBENZOIC ACID
L-Homocystine
Dimethylaminoacethyhydrazide hydrochloride
N-(二硫代羧基)肌氨酸