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Basic Description
| Synonyms | AC9787 | E-Caffeic acid methyl ester | BDBM50029209 | Caffeic acid, methyl ester | 3-(3,4-Dihydroxy-phenyl)-acrylic acid methyl ester | 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, methyl ester, (E)- | methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate | Meth |
|---|---|
| Specifications & Purity | ≥98%(T) |
| Biochemical and Physiological Mechanisms | Naturally occurring ester of caffeic acid. Antihyperglycemic and antidiabetic effects in vivo. Oncoprotective effects in vitro. |
| Shipped In | Normal |
| Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
- Superclass Phenylpropanoids and polyketides
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Cinnamic acids and derivatives |
| Subclass | Hydroxycinnamic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Coumaric acids and derivatives |
| Alternative Parents | Cinnamic acid esters Styrenes Catechols Fatty acid esters 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Methyl esters Enoate esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Coumaric acid or derivatives - Cinnamic acid ester - Catechol - Styrene - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Fatty acid ester - Fatty acyl - Benzenoid - Monocyclic benzene moiety - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Methyl ester - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Carbonyl group - Organic oxide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
| External Descriptors | alkyl caffeate ester |
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Associated Targets(Human)
APP
Tclin
Amyloid-beta A4 protein (8510 Activities)
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BeWo (124 Activities)
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Calu-1 (518 Activities)
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HL-60 (67320 Activities)
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HT-1080 (3966 Activities)
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LoVo (4724 Activities)
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M14 (47487 Activities)
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SiHa (2051 Activities)
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A549 (127892 Activities)
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A-431 (6446 Activities)
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NCI-H1299 (3248 Activities)
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NCI-H157 (619 Activities)
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NCI-H292 (733 Activities)
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HCT-116 (91556 Activities)
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HepG2 (196354 Activities)
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NCI-H460 (60772 Activities)
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KB (17409 Activities)
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LNCaP (8286 Activities)
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LOX IMVI (44321 Activities)
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HOP-62 (47048 Activities)
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HeLa (62764 Activities)
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NCI-H1792 (313 Activities)
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Associated Targets(non-human)
Ttr
Transthyretin (14 Activities)
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Cryz
Quinone oxidoreductase (288 Activities)
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pol
Human immunodeficiency virus type 1 integrase (9041 Activities)
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Mycobacterium tuberculosis (203094 Activities)
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Plasmodium falciparum (966862 Activities)
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Candida albicans (78123 Activities)
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Mus musculus (284745 Activities)
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3T3-L1 (3664 Activities)
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B16 (5829 Activities)
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RAW264.7 (28094 Activities)
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HT-22 (3261 Activities)
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Names and Identifiers
| Pubchem Sid | 488191143 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/488191143 |
| IUPAC Name | methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
| INCHI | InChI=1S/C10H10O4/c1-14-10(13)5-3-7-2-4-8(11)9(12)6-7/h2-6,11-12H,1H3/b5-3+ |
| InChIKey | OCNYGKNIVPVPPX-HWKANZROSA-N |
| Smiles | COC(=O)C=CC1=CC(=C(C=C1)O)O |
| Isomeric SMILES | COC(=O)/C=C/C1=CC(=C(C=C1)O)O |
| Alternate CAS | 67667-67-8 |
| Molecular Weight | 194.19 |
| Reaxy-Rn | 2100051 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2100051&ln= |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 F2523523 |
Certificate of Analysis | May 26, 2025 | M158462 |
| F2523522 |
Certificate of Analysis | May 26, 2025 | M158462 |
| E2429557 |
Certificate of Analysis | May 11, 2024 | M158462 |
| E2429556 |
Certificate of Analysis | May 11, 2024 | M158462 |
| F23271084 |
Certificate of Analysis | Apr 20, 2023 | M158462 |
| F23271085 |
Certificate of Analysis | Apr 20, 2023 | M158462 |
| A2331186 |
Certificate of Analysis | Feb 03, 2023 | M158462 |
| K2222568 |
Certificate of Analysis | Oct 28, 2022 | M158462 |
| K2222572 |
Certificate of Analysis | Oct 28, 2022 | M158462 |
| K2222571 |
Certificate of Analysis | Oct 28, 2022 | M158462 |
| K2222567 |
Certificate of Analysis | Oct 28, 2022 | M158462 |
| H1821124 |
Certificate of Analysis | Jun 20, 2022 | M158462 |
| C2205479 |
Certificate of Analysis | Feb 14, 2022 | M158462 |
| C2205483 |
Certificate of Analysis | Feb 14, 2022 | M158462 |
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Chemical and Physical Properties
| Melt Point(°C) | 160℃ |
|---|---|
| Molecular Weight | 194.180 g/mol |
| XLogP3 | 1.500 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Exact Mass | 194.058 Da |
| Monoisotopic Mass | 194.058 Da |
| Topological Polar Surface Area | 66.800 Ų |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Complexity | 224.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 1 |
| Covalently-Bonded Unit Count | 1 |
Citations of This Product
| 1. Guanghe Zhao, Ruifen Zhang, Lihong Dong, Mei Deng, Yanxia Chen, Mingwei Zhang. (2023) The effects of different enzymes on the liberation of bound phenolics from rice bran dietary fibre and their antioxidant activities. Food Bioscience, 56 (103449). |
| 2. Yueqin Li, Yunzhen Zhang, Lezhen Dong, Ying Li, Yahui Liu, Yang Liu, Lingyi Liu, Lianliang Liu. (2024) Fermentation of Lactobacillus fermentum NB02 with feruloyl esterase production increases the phenolic compounds content and antioxidant properties of oat bran. FOOD CHEMISTRY, 437 (137834). |
| 3. Jian Yao, Lun Gui, Qizhang Long. (2022) A chlorogenic acid esterase from a metagenomic library with unique substrate specificity and its application in caffeic and ferulic acid production from agricultural byproducts. BIOCATALYSIS AND BIOTRANSFORMATION, |
| 4. Guanghe Zhao, Ruifen Zhang, Lihong Dong, Lei Liu, Fei Huang, Xuchao Jia, Mei Deng, Jianwei Chi, Yongxuan Ma, Yanxia Chen, Qin Ma, Mingwei Zhang. (2022) Bound phenolics in rice bran dietary fibre released by different chemical hydrolysis methods: content, composition and antioxidant activities. INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY, 57 (9): (5909-5916). |
| 5. Shuai Zhang, Qin Ma, Lihong Dong, Xuchao Jia, Lei Liu, Fei Huang, Guang Liu, Zhida Sun, Jianwei Chi, Mingwei Zhang, Ruifen Zhang. (2022) Phenolic profiles and bioactivities of different milling fractions of rice bran from black rice. FOOD CHEMISTRY, 378 (132035). |
| 6. Yao Jian, Gui Lun, Yin Shaocheng. (2021) A novel esterase from a soil metagenomic library displaying a broad substrate range. AMB Express, 11 (1): (1-10). |
| 7. Weiyue Liang, Tianzhen Xiong, Xiaomei Wang, Huaxiang Deng, Yajun Bai, Tai-Ping Fan, Xiaohui Zheng, Yujie Cai. (2020) A novel feruloyl esterase with high rosmarinic acid hydrolysis activity from Bacillus pumilus W3. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 161 (525). |
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