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Basic Description
| Synonyms | DTXSID501009309 | Isoferulate | XSQ2K2G7MC | (E)-3-(3-hydroxy-4-methoxyphenyl)acrylicacid | DTXCID90908460 | Hesperetic acid | SCHEMBL249042 | 2-Propenoic acid, 3-(3-hydroxy-4-methoxyphenyl)- | 3-(3-Hydroxy-4-methoxyphenyl)acrylic acid | trans-Isoferulic |
|---|---|
| Specifications & Purity | Moligand™, ≥98% |
| Biochemical and Physiological Mechanisms | 3-Hydroxy-4-methoxycinnamic acid is bioactive metabolite of Spilanthes acmella Murr. It increases the resistance of low-density lipoprotein (LDL) to oxidation. |
| Storage Temp | Store at 2-8°C |
| Shipped In |
Wet ice This product requires cold chain shipping. Ground and other economy services are not available. |
| Grade | Moligand™ |
| Product Description |
3-Hydroxy-4-methoxycinnamic acid is isolated from the aerial part of Artemisia capillaris, Chinese medicinal plant. It is a component of chinese herbal medicine used for a pain killer and stomachic. |
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 | Hydroxycinnamic acids |
| Alternative Parents | Coumaric acids and derivatives Cinnamic acids Methoxyphenols Styrenes Phenoxy compounds Methoxybenzenes Anisoles Alkyl aryl ethers 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Cinnamic acid - Coumaric acid or derivatives - Hydroxycinnamic acid - Methoxyphenol - Phenoxy compound - Anisole - Methoxybenzene - Styrene - Phenol ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Phenol - Monocyclic benzene moiety - Benzenoid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Ether - Organic oxygen compound - Carbonyl group - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroxycinnamic acids. These are compounds containing an cinnamic acid where the benzene ring is hydroxylated. |
| External Descriptors | ferulic acids |
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Associated Targets(Human)
PMVK
Tchem
Phosphomevalonate kinase (1 Activities)
| Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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ESR1
Tclin
Estrogen receptor alpha (17718 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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TYR
Tclin
Tyrosinase (717 Activities)
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HT-1080 (3966 Activities)
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A549 (127892 Activities)
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HeLa (62764 Activities)
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HYAL1
Tbio
Hyaluronidase-1 (8 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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GNAS
Tbio
Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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TDP1
Tchem
Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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CBX1
Tbio
Chromobox protein homolog 1 (92434 Activities)
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Associated Targets(non-human)
Ralstonia solanacearum (520 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Trypanosoma brucei brucei (13300 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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RAW264.7 (28094 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 | 504760044 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504760044 |
| IUPAC Name | (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid |
| INCHI | InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ |
| InChIKey | QURCVMIEKCOAJU-HWKANZROSA-N |
| Smiles | COC1=C(C=C(C=C1)C=CC(=O)O)O |
| Isomeric SMILES | COC1=C(C=C(C=C1)/C=C/C(=O)O)O |
| WGK Germany | 2 |
| RTECS | UD3365400 |
| Molecular Weight | 194.18 |
| Beilstein | 10437 |
| Reaxy-Rn | 2212758 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2212758&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 |
|---|---|---|---|
 K2224525 |
Certificate of Analysis | Aug 19, 2022 | I131024 |
| K2224891 |
Certificate of Analysis | Aug 19, 2022 | I131024 |
| K2224522 |
Certificate of Analysis | Aug 19, 2022 | I131024 |
| I1428145 |
Certificate of Analysis | Jul 19, 2022 | I131024 |
| H1801077 |
Certificate of Analysis | Jun 11, 2022 | I131024 |
| H1801076 |
Certificate of Analysis | Jun 11, 2022 | I131024 |
Chemical and Physical Properties
| Melt Point(°C) | 230°C |
|---|---|
| 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. Li Min, Wang Yayao, Xiao Jianxing, Yan Xingfu, Liu Bingru. (2023) Allelopathic inhibition effects and mechanism of phenolic acids to Microcystis aeruginosa. ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH, 30 (15): (45388-45397). |
| 2. 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). |
| 3. Fengjie Yu, Jianing Zhang, Yunmin Tao, Chunping Du, Wenchao Yang, Wenbin Chen, Xijuan Tu. (2021) High-throughput subzero-temperature assisted homogenous liquid-liquid extraction for the fast sample preparation of multiple phenolic compounds in propolis. JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1179 (122823). |
| 4. Haiying Cai, Qi Zhang, Lingzhi Shen, Jie Luo, Ruiyu Zhu, Jianwei Mao, Minjie Zhao, Chenggang Cai. (2019) Phenolic profile and antioxidant activity of Chinese rice wine fermented with different rice materials and starters. LWT-FOOD SCIENCE AND TECHNOLOGY, 111 (226). |
| 5. Wenbin Chen, Xijuan Tu, Dehui Wu, Zhaosheng Gao, Siyuan Wu, Shaokang Huang. (2019) Comparison of the Partition Efficiencies of Multiple Phenolic Compounds Contained in Propolis in Different Modes of Acetonitrile–Water-Based Homogenous Liquid–Liquid Extraction. MOLECULES, 24 (3): (442). |
| 6. Yang Lu, Shuhua Shan, Hanqing Li, Jiangying Shi, Xiaoli Zhang, Zhuoyu Li. (2018) Reversal Effects of Bound Polyphenol from Foxtail Millet Bran on Multidrug Resistance in Human HCT-8/Fu Colorectal Cancer Cell. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 66 (20): (5190–5199). |
| 7. Han Peng, Zeyuan Deng, Xuan Chen, Yong Sun, Bing Zhang, Hongyan Li. (2018) Major chemical constituents and antioxidant activities of different extracts from the peduncles of Hovenia acerba Lindl. INTERNATIONAL JOURNAL OF FOOD PROPERTIES, |
| 8. Han Peng, Wenting Li, Hongyan Li, Zeyuan Deng, Bing Zhang. (2017) Extractable and non-extractable bound phenolic compositions and their antioxidant properties in seed coat and cotyledon of black soybean (Glycinemax (L.) merr). Journal of Functional Foods, 32 (296). |
| 9. Lei Liu, Jinjie Guo, Ruifen Zhang, Zhencheng Wei, Yuanyuan Deng, Jinxin Guo, Mingwei Zhang. (2015) Effect of degree of milling on phenolic profiles and cellular antioxidant activity of whole brown rice. FOOD CHEMISTRY, 185 (318). |
| 10. Houmei Liu, Xiaojing Liang, Xusheng Wang, Yong Guo, Xia Liu. (2014) Polyelectrolyte assembled graphene oxide coated silica composite as sorbent for solid-phase extraction of cinnamic acid and its derivatives. RSC Advances, 5 (6): (4420-4427). |
| 11. Haisha Yang, Yuqiong Dong, Huijing Du, Haiming Shi, Yunhua Peng, Xiaobo Li. (2011) Antioxidant Compounds from Propolis Collected in Anhui, China. MOLECULES, 16 (4): (3444-3455). |
| 12. Shi Shen,Jingbo Wang,Qin Zhuo,Xi Chen,Tingting Liu,Shuang-Qing Zhang. (2018-05-09) Quantitative and Discriminative Evaluation of Contents of Phenolic and Flavonoid and Antioxidant Competence for Chinese Honeys from Different Botanical Origins.. Molecules (Basel, Switzerland), 23 ((5)): |
| 13. Xiaoqin La, Xiaoting He, Jingyi Liang, Zhaoyan Zhang, Hanqing Li, Yizhi Liu, Ting Liu, Zhuoyu Li, Changxin Wu. (2024) Gastroprotective Effect of Isoferulic Acid Derived from Foxtail Millet Bran against Ethanol-Induced Gastric Mucosal Injury by Enhancing GALNT2 Enzyme Activity. Nutrients, 16 (13): (2148). |
| 14. Min Li, Zhen-Fang Shang, Zhi-Jing Ni, Hui-Jun Zhao, Qian Lei, Zhao-Jun Wei. (2024) Growth and metabolism regulation of cinnamic acid and its derivatives to Auxenochlorella pyrenoidosa. Algal Research-Biomass Biofuels and Bioproducts, 84 (103742). |
| 15. Kunying Nie, Jiali Zhang, Haitao Xu, Keyun Ren, Chunlei Yu, Qi Zhang, Falan Li, Qingqing Yang. (2024) Reverse design of haptens based on antigen spatial conformation to prepare anti-capsaicinoids&gingerols antibodies for monitoring of gutter cooking oil. Food Chemistry-X, 22 (101273). |
| 16. Haoping Liu, Hua Zhang, Mengting Geng, Dingxin Shi, Dongsheng Liu, Yanxiao Jiao, Zhiqiang Lei, You Peng. (2025) The Impact of Cooking on Antioxidant and Enzyme Activities in Ruichang Yam Polyphenols. Foods, 14 (1): (14). |
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