Α-氰-4-羟基肉桂酸
ALPHA-CYANO-4-HYDROXYCINNAMIC ACID
CAS: 28166-41-8
Molecular Formula: C10H7NO3
Α-氰-4-羟基肉桂酸 - Names and Identifiers
| Name | ALPHA-CYANO-4-HYDROXYCINNAMIC ACID |
| Synonyms | ACCA 4-HCCA ALPHA-CCA ALPHA-CHCA ALPHA-CYANO LABOTEST-BB LT00159295 α-Cyano-4-hydroxycinnamic acid ALPHA-CYANO-4-HYDROXYCINNAMIC ACID |
| CAS | 28166-41-8 |
| EINECS | 248-879-1 |
| InChIKey | AFVLVVWMAFSXCK-VMPITWQZSA-N |
Α-氰-4-羟基肉桂酸 - Physico-chemical Properties
| Molecular Formula | C10H7NO3 |
| Molar Mass | 189.17 |
| Density | 1.3175 (rough estimate) |
| Melting Point | 有机试剂 |
| Boling Point | 324.41°C (rough estimate) |
| Solubility | methanol: 10 mg/mL, clear |
| Appearance | powder |
| Color | yellow |
| BRN | 3271427 |
| pKa | 0.85±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.5400 (estimate) |
| MDL | MFCD00004204 |
| Physical and Chemical Properties | Bioactivity 4-Chloro-α-cyanocinnamic acid (α-CHCA) is a classic monocarboxylate transporters (MCT) inhibitor. Compared with the effect on other MCTs, α-cyano-4-hydroxycinnamate (CHC) has a higher selectivity for MCT1 (10 times more than for other MCTs). |
| Use | Uses 2-cyano-4-hydroxy (CHC) is a useful research chemical. CHC is a common organic matrix assisted laser desorption/ionization (MALDI) matrix. CHC is sublimated directly without decomposition. |
Α-氰-4-羟基肉桂酸 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29269090 |
Α-氰-4-羟基肉桂酸 - Reference
| Reference Show more | 1. [IF=6.986] Shuai Guo et al."Enhancement of On-tissue Chemical Derivatization by Laser-Assisted Tissue Transfer for MALDI MS Imaging."Anal Chem. 2020;92(1):1431–1438 |
Α-氰-4-羟基肉桂酸 - Uses and synthesis methods
Target
Target Value
MCT
in vitro studies
Most glioma cells are sensitive to CHC, except for SW1088 and SW1783 cells (which are less sensitive to CHC). The effect of CHC on U251 and SW1080 cell biomass was correlated with its lactate transport activity. U251 cells have higher MCT1 and CD147 levels on the plasma membrane than SW1088 cells, so CHC reduces glucose consumption and lactic acid production in U251 cells, while there is no such effect in SW1088. In sensitive U251 cells, CHC can inhibit cell proliferation and induce cell death, which has cytotoxic effect. However, in low-sensitive SW1088 cells, CHC only inhibits cell proliferation, but does not induce cell death, and has the effect of inhibiting cell growth. CHC does not enter the cell, and its inhibitory effect depends on interaction with extracellular on-membrane proteins. CHC can inhibit different MCT subtypes, however, their selectivity and sensitivity are different. In addition to MCT1,CHC can also inhibit MCT4 activity. However, inhibition of MCT4 activity requires a higher concentration of compounds because the binding affinity of CHC to MCT4 is lower (5-10 times the interaction between MCT1 and CHC at Ki value; 50-100 mM). MCT1, 2, 4-mediated transport can be competitively inhibited by CHC, whereas MCT3-mediated transport is insensitive to this inhibitor. CHC is also a small molecule inhibitor of lactic acid transport.
In vivo studies
In normal brain tissue, CHC has little effect. There was no significant effect on neuronal lactate shuttle.
Last Update：2024-04-09 21:54:55
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