Structure of Sesamin
CAS No.: 607-80-7
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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.
Sesamin is a natural product derived from sesame seeds, acting as a potent serum lipid-lowering food component.
Synonyms: Fagarol; Fsesamin; Sezamin
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 607-80-7 |
Formula : | C20H18O6 |
M.W : | 354.35 |
SMILES Code : | [H][C@]12[C@]([C@@H](C3=CC=C(OCO4)C4=C3)OC2)([H])CO[C@@H]1C5=CC=C6OCOC6=C5 |
Synonyms : |
Fagarol; Fsesamin; Sezamin
|
MDL No. : | MFCD00216134 |
InChI Key : | PEYUIKBAABKQKQ-AFHBHXEDSA-N |
Pubchem ID : | 72307 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
Yeast cells | 100 µM | 48 hours | SrCYP92B14 oxidized (+)-sesamin primarily to (+)-sesaminol, with minimal production of (+)-sesamolin. | PMC7756453 |
Yeast cells | 100 µM | 60 min | Failed to catalyze the reaction | PMC5735135 |
BV-2 cells | 1, 10, 50 μM | 24 hours | Sesamin protected BV-2 cells from KA-induced injury by reducing LDH release and increasing cell viability | PMC3129306 |
PC12 cells | 0.1, 0.5, 1.0, 2.0 μM | 24 hours | Sesamin protected PC12 cells from KA-induced injury by reducing LDH release and increasing cell viability | PMC3129306 |
BEnd.3 cells | 50 μmol/L | 1 hour | To evaluate the protective effect of sesamin in alleviating the loss of ZO-1 induced by stretch injury. Sesamin pretreatment significantly alleviated the loss of ZO-1 in bEnd.3 cells after stretch injury. | PMC5672062 |
Human bone marrow mesenchymal stem cells (BMSCs) | 0.5 μM | 24 hours | Sesamin regulated chondrogenesis of BMSCs by activating ERα signaling and downstream BMP2 and SOX9 expression. | PMC9147588 |
Human umbilical vein endothelial cells (HUVECs) | 0.5 μM | 3 and 6 hours | Sesamin significantly promoted in vitro tube formation activity of HUVECs, and this promoting effect was attenuated by ERα inhibitor. | PMC9147588 |
Human skin fibroblasts (Hs68 cells) | 10 μM and above | Sesamin significantly inhibited UVB-induced intracellular ROS generation at concentrations of 10 μM and above. | PMC6769638 | |
Human skin fibroblasts (Hs68 cells) | 5–50 μM | Sesamin showed no cytotoxicity to Hs68 cells at concentrations of 5–50 μM, with cell viability over 95%. | PMC6769638 | |
MIN6 cells | 50 or 100 μM | 24 hours | To investigate the effects of sesamin on AGEs-induced insulin secretion, cell apoptosis, ROS production, and NADPH oxidase expression and activity in MIN6 cells. Results showed that sesamin significantly ameliorated AGEs-induced insulin secretion defects, reduced cell apoptosis and ROS production, and downregulated NADPH oxidase expression and activity. | PMC4488808 |
RAW264.7 cells | 0-10 μM | 3 days | Sesamin inhibits osteoclastogenic differentiation of RAW264.7 cells by deactivating NF-κB signaling pathway. | PMC8704418 |
Mouse bone marrow mesenchymal stem cells (BMSCs) | 1-10 μM | 3 days | Sesamin promotes osteogenic differentiation of BMSCs by activating Wnt/β-catenin signaling pathway. | PMC8704418 |
NIT-1 pancreatic β-cells | 400, 200, 100 µg/mL | 24 hours | Sesamin significantly reversed STZ-induced NIT-1 cell viability loss, increased insulin secretion, enhanced SOD, GSHpx activities and GSH content, reduced MDA, NO, NOS, and iNOS levels, and improved cell morphology. | PMC3546733 |
GH3 cells | 10 µM | Sesamin further suppressed the CBN-induced decrease in peak INa amplitude | PMC7827714 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
FVB mice and Sprague-Dawley rats | KA-induced status epilepticus model | Oral | 15 mg/kg or 30 mg/kg | Once daily for 3 days | Sesamin significantly reduced KA-induced oxidative stress and mortality, and increased plasma α-tocopherol levels | PMC3129306 |
Mice | CCl4-induced liver injury model | Oral (sesamin), Intraperitoneal (SC1) | 25 mg/kg | Twice administration (1 h before and 7 h after CCl4 injection) | Sesamin and SC1 significantly suppressed CCl4-induced elevation of liver injury markers (AST, ALT, LDH) and inflammatory responses (TNFα, MCP-1), and these effects were abolished in ANX A1 knockout mice. | PMC7033200 |
C57BL/6 mice | Traumatic brain injury (TBI) model | Intraperitoneal injection | 30 mg/kg/d | Once daily until the animals were sacrificed | To evaluate the protective function of sesamin on BBB disruption after TBI. Sesamin treatment significantly attenuated CCI-induced brain edema, tissue hemoglobin levels, Evans blue extravasation, and AQP4 expression levels, and significantly alleviated CCI-induced loss of tight junction proteins ZO-1 and occludin. | PMC5672062 |
C57BL/6 mice | Osteoporotic fracture model | Oral gavage | 80 mg/kg/day | Once daily for 14 or 28 days | Sesamin markedly improved callus formation and increased the cartilaginous area at the early-stage, as well as narrowed the fracture gap and expanded callus volume at the late-stage fracture healing site of the OVX mice femur. Furthermore, the angiogenesis at the osteoporotic fracture site was also significantly improved by sesamin treatment. | PMC9147588 |
Hairless mice (BALB/cAnN.Cg-Foxn1nu/CrlNarl) | UVB-induced skin photodamage model | Topical application | 50 μM and 200 μM | Once daily for 10 weeks | Sesamin significantly reduced UVB-induced skin erythema, inflammation, and wrinkle formation, and restored skin collagen content. | PMC6769638 |
C57BL/6J mice | AGEs-induced pancreatic β-cell dysfunction and apoptosis model | Oral | 160 mg/kg body weight | Once daily for four weeks | To investigate the protective effects of sesamin on AGEs-induced pancreatic β-cell dysfunction and apoptosis. Results showed that sesamin significantly improved AGEs-induced glucose intolerance and insulin secretion defects, reduced pancreatic β-cell apoptosis and ROS production. | PMC4488808 |
C57BL/6 mice | Ovariectomy (OVX)-induced osteoporosis model | Oral | 80 mg/kg and 160 mg/kg | Once daily for two months | Sesamin attenuates bone loss in OVX mice osteoporosis model via down-regulating DANCR expression. | PMC8704418 |
Mice | Acetic acid-induced writhing response model | Oral | 50, 100, 200 mg/kg | Single dose, 60 minutes before acetic acid injection | To evaluate the analgesic activity of sesamin, results showed that sesamin at 200 mg/kg significantly inhibited acetic acid-induced abdominal writhing | PMC4042560 |
Tags: Sesamin | delta | desaturase | polyunsaturated | fatty | acid | biosynthesis | neuroprotection | cerbral | ischemia | 607-80-7
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
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Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
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. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
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. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
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: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
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. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
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. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
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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