Structure of Esculetin
CAS No.: 305-01-1
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Esculetin is a naturally occuring 5-lipoxygenase and 12-Lipoxygenase inhibitor with IC50 values of ID50 values of 4 and 2.5 µM, respectively.
Synonyms: Cichorigenin; Aesculetin; NSC 26428
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| CAS No. : | 305-01-1 |
| Formula : | C9H6O4 |
| M.W : | 178.14 |
| SMILES Code : | O=C1C=CC2=C(O1)C=C(O)C(O)=C2 |
| Synonyms : |
Cichorigenin; Aesculetin; NSC 26428
|
| MDL No. : | MFCD00006874 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Target |
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In Vitro:
|
Cell Line
|
Concentration | Treated Time | Description | References |
| colonic crypt epithelium | 500 μM | 10 minutes | Completely abolished DOC-induced increases in chemiluminescence (CL) | J Clin Invest. 1986 Mar;77(3):850-9 |
| colonic mucosal scrapings | 100 μM | 10 minutes | Suppressed basal and DOC-induced increases in chemiluminescence (CL) by 40-50%, and reduced accumulation of PGE2, LTB4, 5-HETE, 12-HETE, and 15-HETE | J Clin Invest. 1986 Mar;77(3):850-9 |
| Sorted ATMs | 25 μg/mL DIL-ox-LDL | 24 hours | Esculetin significantly increased the percentage of CD36+ cells and CD36+ DIL-ox-LDL+ cells, indicating enhanced phagocytosis in ATMs. | Theranostics. 2025 Apr 28;15(12):5910-5930 |
| RAW 264.7 cells | 25 μg/mL DIL-ox-LDL | 3 to 24 hours | Esculetin significantly increased the fluorescence intensity of intracellular DIL-ox-LDL, indicating enhanced phagocytosis in macrophages. | Theranostics. 2025 Apr 28;15(12):5910-5930 |
| PC12 cells | 25 μM or 50 μM | 24 hours | Esculetin functions as an ERR agonist, enhancing glycolysis and mitochondrial respiration, leading to elevated cellular ATP levels | EBioMedicine. 2017 Aug;22:225-241 |
| Bovine chondrocytes | 31 μM–500 μM | 6 days | Esculetin inhibited IL-1-induced cartilage degradation and significantly blocked the accumulation of ADAMTS4 and MT4-MMP proteins | Osteoarthritis Cartilage. 2005 Apr;13(4):269-77 |
| T/C28a4 chondrocytes | 100–500 µM | 24 hours | To evaluate the inhibitory effect of Esculetin on MMP-1, MMP-3, and MMP-13 mRNA expression. Results showed that 250 µM EST reduced MMP-1, MMP-3, and MMP-13 mRNA expression to control levels, while TIMP-1 mRNA levels were unaffected. | Ann Rheum Dis. 2001 Feb;60(2):158-65 |
| Human articular cartilage cells | 50–500 µM | 21 days | To evaluate the inhibitory effect of Esculetin on IL1 á and OSM-induced degradation in human articular cartilage. Results showed that 50 µM EST significantly inhibited proteoglycan and collagen degradation (p<0.01) and reduced MMP-1 levels (p<0.001). | Ann Rheum Dis. 2001 Feb;60(2):158-65 |
| Bovine nasal cartilage cells | 10–330 µM | 14 days | To evaluate the inhibitory effect of Esculetin on IL1 á and OSM-induced collagen and proteoglycan degradation. Results showed that 66 µM EST significantly inhibited collagen degradation (p<0.001), and 100 µM EST significantly inhibited proteoglycan degradation (p<0.05). | Ann Rheum Dis. 2001 Feb;60(2):158-65 |
| Phytophthora sojae zoospores | 100 μM | 30 min | To evaluate the inhibitory effect of Esculetin on the chemotaxis of Phytophthora sojae zoospores. Results showed that Esculetin competitively binds to the PsIRK1 receptor, disrupting zoospore chemotaxis toward genistein and thereby inhibiting infection. | Sci Adv. 2025 Jan 10;11(2):eadt0925 |
In Vivo:
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Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
| Sprague-Dawley rats | Colonic epithelial proliferation model | Intracolonic instillation | 50 μmol (25 mM) | Single administration, observed at 4 hours (ODC activity) or 24 hours ([3H]TdR incorporation) | Inhibited DOC-induced increases in ornithine decarboxylase (ODC) activity and [3H]TdR incorporation into DNA | J Clin Invest. 1986 Mar;77(3):850-9 |
| C57BL6J male mice | High-fat diet-induced postprandial dyslipidemia model | Oral gavage | 30, 90, 180 mg/kg/d | Once daily for 7 days | Esculetin significantly elevated postprandial HDL cholesterol levels and increased bile acid content in bile, promoting cholesterol excretion. | Theranostics. 2025 Apr 28;15(12):5910-5930 |
| C57BL/6N Slc mice | MPTP-induced Parkinson's disease model | Oral | 50 mg/kg/day | 4 days per week for 5 months | Esculetin protected dopaminergic neurons by maintaining ATP levels and reducing ER stress, mitigating Parkinson's disease symptoms | EBioMedicine. 2017 Aug;22:225-241 |
| Soybean (Glycine max) | Soybean seedlings | Root dipping | 100 μM | Single treatment, lasting 30 minutes | To evaluate the preventive effect of Esculetin on Phytophthora sojae infection in soybean seedlings. Results showed that Esculetin treatment significantly increased the survival rate of soybean seedlings and reduced pathogen biomass in the roots. | Sci Adv. 2025 Jan 10;11(2):eadt0925 |
Tags: Esculetin | PI3K | Akt | Phosphoinositide 3-kinase | PKB | Protein kinase B | 305-01-1 |
Precautionary Statements-General | |
| Code | Phrase |
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| Code | Phrase |
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| P220 | Keep/Store away from clothing/combustible materials. |
| P221 | Take any precaution to avoid mixing with combustibles |
| P222 | Do not allow contact with air. |
| P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
| P230 | Keep wetted |
| P231 | Handle under inert gas. |
| P232 | Protect from moisture. |
| P233 | Keep container tightly closed. |
| P234 | Keep only in original container. |
| P235 | Keep cool |
| P240 | Ground/bond container and receiving equipment. |
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| P263 | Avoid contact during pregnancy/while nursing. |
| P264 | Wash hands thoroughly after handling. |
| P265 | Wash skin thouroughly after handling. |
| P270 | Do not eat, drink or smoke when using this product. |
| P271 | Use only outdoors or in a well-ventilated area. |
| P272 | Contaminated work clothing should not be allowed out of the workplace. |
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| P281 | Use personal protective equipment as required. |
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| P283 | Wear fire/flame resistant/retardant clothing. |
| P284 | Wear respiratory protection. |
| P285 | In case of inadequate ventilation wear respiratory protection. |
| P231 + P232 | Handle under inert gas. Protect from moisture. |
| P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
| Code | Phrase |
| P301 | IF SWALLOWED: |
| P304 | IF INHALED: |
| P305 | IF IN EYES: |
| P306 | IF ON CLOTHING: |
| P307 | IF exposed: |
| P308 | IF exposed or concerned: |
| P309 | IF exposed or if you feel unwell: |
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| P311 | Call a POISON CENTER or doctor/physician. |
| P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
| P313 | Get medical advice/attention. |
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| P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
| P321 | |
| P322 | |
| P330 | Rinse mouth. |
| P331 | Do NOT induce vomiting. |
| P332 | IF SKIN irritation occurs: |
| P333 | If skin irritation or rash occurs: |
| P334 | Immerse in cool water/wrap n wet bandages. |
| P335 | Brush off loose particles from skin. |
| P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
| P337 | If eye irritation persists: |
| P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
| P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P342 | If experiencing respiratory symptoms: |
| P350 | Gently wash with plenty of soap and water. |
| P351 | Rinse cautiously with water for several minutes. |
| P352 | Wash with plenty of soap and water. |
| P353 | Rinse skin with water/shower. |
| P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
| P361 | Remove/Take off immediately all contaminated clothing. |
| P362 | Take off contaminated clothing and wash before reuse. |
| P363 | Wash contaminated clothing before reuse. |
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| P371 | In case of major fire and large quantities: |
| P372 | Explosion risk in case of fire. |
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| P374 | Fight fire with normal precautions from a reasonable distance. |
| P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
| P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
| P378 | |
| P380 | Evacuate area. |
| P381 | Eliminate all ignition sources if safe to do so. |
| P390 | Absorb spillage to prevent material damage. |
| P391 | Collect spillage. Hazardous to the aquatic environment |
| P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
| P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
| P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
| P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
| P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
| P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
| P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
| P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
| P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
| P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
| P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
| P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
| P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
| P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
| P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
| P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
| P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
| P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
| P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
| P370 + P376 | In case of fire: Stop leak if safe to Do so. |
| P370 + P378 | In case of fire: |
| P370 + P380 | In case of fire: Evacuate area. |
| P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
| P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
| Code | Phrase |
| P401 | |
| P402 | Store in a dry place. |
| P403 | Store in a well-ventilated place. |
| P404 | Store in a closed container. |
| P405 | Store locked up. |
| P406 | Store in corrosive resistant/ container with a resistant inner liner. |
| P407 | Maintain air gap between stacks/pallets. |
| P410 | Protect from sunlight. |
| P411 | |
| P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
| P413 | |
| P420 | Store away from other materials. |
| P422 | |
| P402 + P404 | Store in a dry place. Store in a closed container. |
| P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
| P403 + P235 | Store in a well-ventilated place. Keep cool. |
| P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
| P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
| P411 + P235 | Keep cool. |
Disposal | |
| Code | Phrase |
| P501 | Dispose of contents/container to ... |
| P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
| Code | Phrase |
| H200 | Unstable explosive |
| H201 | Explosive; mass explosion hazard |
| H202 | Explosive; severe projection hazard |
| H203 | Explosive; fire, blast or projection hazard |
| H204 | Fire or projection hazard |
| H205 | May mass explode in fire |
| H220 | Extremely flammable gas |
| H221 | Flammable gas |
| H222 | Extremely flammable aerosol |
| H223 | Flammable aerosol |
| H224 | Extremely flammable liquid and vapour |
| H225 | Highly flammable liquid and vapour |
| H226 | Flammable liquid and vapour |
| H227 | Combustible liquid |
| H228 | Flammable solid |
| H229 | Pressurized container: may burst if heated |
| H230 | May react explosively even in the absence of air |
| H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
| H240 | Heating may cause an explosion |
| H241 | Heating may cause a fire or explosion |
| H242 | Heating may cause a fire |
| H250 | Catches fire spontaneously if exposed to air |
| H251 | Self-heating; may catch fire |
| H252 | Self-heating in large quantities; may catch fire |
| H260 | In contact with water releases flammable gases which may ignite spontaneously |
| H261 | In contact with water releases flammable gas |
| H270 | May cause or intensify fire; oxidizer |
| H271 | May cause fire or explosion; strong oxidizer |
| H272 | May intensify fire; oxidizer |
| H280 | Contains gas under pressure; may explode if heated |
| H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
| H290 | May be corrosive to metals |
Health hazards | |
| Code | Phrase |
| H300 | Fatal if swallowed |
| H301 | Toxic if swallowed |
| H302 | Harmful if swallowed |
| H303 | May be harmful if swallowed |
| H304 | May be fatal if swallowed and enters airways |
| H305 | May be harmful if swallowed and enters airways |
| H310 | Fatal in contact with skin |
| H311 | Toxic in contact with skin |
| H312 | Harmful in contact with skin |
| H313 | May be harmful in contact with skin |
| H314 | Causes severe skin burns and eye damage |
| H315 | Causes skin irritation |
| H316 | Causes mild skin irritation |
| H317 | May cause an allergic skin reaction |
| H318 | Causes serious eye damage |
| H319 | Causes serious eye irritation |
| H320 | Causes eye irritation |
| H330 | Fatal if inhaled |
| H331 | Toxic if inhaled |
| H332 | Harmful if inhaled |
| H333 | May be harmful if inhaled |
| H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
| H335 | May cause respiratory irritation |
| H336 | May cause drowsiness or dizziness |
| H340 | May cause genetic defects |
| H341 | Suspected of causing genetic defects |
| H350 | May cause cancer |
| H351 | Suspected of causing cancer |
| H360 | May damage fertility or the unborn child |
| H361 | Suspected of damaging fertility or the unborn child |
| H361d | Suspected of damaging the unborn child |
| H362 | May cause harm to breast-fed children |
| H370 | Causes damage to organs |
| H371 | May cause damage to organs |
| H372 | Causes damage to organs through prolonged or repeated exposure |
| H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
| Code | Phrase |
| H400 | Very toxic to aquatic life |
| H401 | Toxic to aquatic life |
| H402 | Harmful to aquatic life |
| H410 | Very toxic to aquatic life with long-lasting effects |
| H411 | Toxic to aquatic life with long-lasting effects |
| H412 | Harmful to aquatic life with long-lasting effects |
| H413 | May cause long-lasting harmful effects to aquatic life |
| H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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