CAS No. :	480-39-7
Formula :	C₁₅H₁₂O₄
M.W :	256.25
SMILES Code :	O=C1C[C@@H](C2=CC=CC=C2)OC3=CC(O)=CC(O)=C13
Synonyms :	(+)-Pinocoembrin; Dihydrochrysin; NSC 279005
MDL No. :	MFCD06858345
InChI Key :	URFCJEUYXNAHFI-ZDUSSCGKSA-N
Pubchem ID :	68071

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Primary microglia	1, 3, 10 µM	1 hour pretreatment followed by 24 hours LPS stimulation	Pinocembrin dose-dependently inhibited the secretion of proinflammatory cytokines (TNF-α, IL-1β, and IL-6) and reduced NO production in LPS-stimulated primary microglia.	Brain Behav Immun. 2017 Mar;61:326-339.
BV-2 cells	1, 3, 10 µM	1 hour pretreatment followed by 24 hours LPS stimulation	Pinocembrin dose-dependently inhibited the secretion of proinflammatory cytokines (TNF-α, IL-1β, and IL-6) and reduced NO production in LPS-stimulated BV-2 cells. Additionally, 10 μM Pinocembrin significantly decreased iNOS expression.	Brain Behav Immun. 2017 Mar;61:326-339.
Keloid fibroblasts	0 to 80 µM	1, 3, 5, 7, and 9 days	To evaluate the effect of pinocembrin on the proliferation of keloid fibroblasts, results showed that pinocembrin dose-dependently inhibited cell proliferation	Biomolecules. 2021 Aug 19;11(8):1240.
SH-SY5Y cells	1.0 µM, 3.0 µM, 10.0 µM	24 hours	To investigate the effect of pinocembrin on cell viability and ROS generation. Results showed that pinocembrin enhanced cell viability but had no significant effect on ROS generation.	BMC Med. 2012 Sep 18;10:105.
U2OS cells	1.0 µM, 3.0 µM, 10.0 µM	24 hours	To investigate the effect of pinocembrin on RAGE expression. Results showed that pinocembrin significantly inhibited the overexpression of RAGE.	BMC Med. 2012 Sep 18;10:105.
BV2 cells	1, 3, 10 µM	24 hours	To evaluate the protective effects of Pinocembrin on BV2 cells treated with intermittent hypoxia (IH). Results showed that Pinocembrin significantly increased cell survival, inhibited NLRP3 inflammasome activation, and enhanced BNIP3-mediated mitophagy.	J Neuroinflammation. 2020 Nov 11;17(1):337.
Y-79 retinoblastoma cells	5 µM	24 hours	Assess the effect of Pinocembrin on TGF-β1-induced invasion and migration abilities of Y-79 cells, showing significant inhibition of invasion and migration	Cell Biosci. 2014 Aug 12;4:41.
Y-79 retinoblastoma cells	0-5 µM	24 hours	Evaluate the cytotoxicity of Pinocembrin on Y-79 cells, showing no cytotoxicity at concentrations ranging from 0-5 μM	Cell Biosci. 2014 Aug 12;4:41.
Mouse primary dermal fibroblasts	20, 40, and 80 µM	24 hours	To evaluate the effect of pinocembrin on TGF-β1-induced proliferation of mouse primary dermal fibroblasts, results showed that pinocembrin significantly inhibited cell proliferation	Biomolecules. 2021 Aug 19;11(8):1240.
SH-SY5Y cells	3, 10, 30 µM	24 hours	To evaluate the protective effect of pinocembrin on SH-SY5Y cells under oxygen-glucose deprivation (OGD) conditions. Results showed that pinocembrin significantly increased the expression levels of Reelin, apoER2, and p-dab1 after OGD injury.	Drug Des Devel Ther. 2020 Sep 4;14:3577-3587.
Cardiac myofibroblasts	25 µM	4 hours	Pinocembrin inhibited collagen secretion and fibrosis	Mol Med. 2021 Sep 6;27(1):100.
Bone marrow macrophages (BMMs)	0, 1, 5, 10, 20, 50 µM	48 hours	Assess the cytotoxicity of PIN on BMMs, showing no significant cytotoxicity at concentrations of 20 μM or lower.	J Orthop Translat. 2024 Mar 27;45:197-210.
Bone marrow macrophages (BMMs)	2.5 and 5 µM	60 minutes	Assess the effect of PIN on RANKL-induced intracellular ROS production, showing a significant reduction in ROS levels.	J Orthop Translat. 2024 Mar 27;45:197-210.
Endothelial cells (ECs)	40 µM	7 days	To evaluate the protective effect of pinocembrin against AGE-induced cytotoxicity. Results showed that pinocembrin restored cell cycle distribution and viability, and significantly reduced AGE-induced oxidative stress.	Cells. 2019 Apr 26;8(5):385.
HUVECs	10, 20, 65 µM	8 hours	To evaluate the effect of Pinocembrin on the ability of HUVECs to form tubular structures. The results showed that Pinocembrin exhibited antiangiogenic activity both in solution and microencapsulated forms.	Pharmaceutics. 2022 Feb 22;14(3):484.

Caenorhabditis elegans	Wild-type N2 and mutants (DR26 daf-16, TJ356, VC475 hsp-16.2, CB1370 daf-2, TJ1052 age-1)	NGM medium administration	200 μM	Transferred to new plates daily until experiment endpoint (e.g., Day 5 for thermal stress, Day 5 for oxidative stress)	Evaluate anti-aging effects of Pinocembrin derivatives (e.g., pb-3): 1) Enhanced thermotolerance and oxidative stress resistance (prolonged median survival time); 2) Reduced lipofuscin accumulation; 3) Decreased intracellular ROS levels; 4) Activated SOD-3 expression and DAF-16 nuclear translocation via DAF-16/FOXO pathway; 5) No lifespan extension in daf-16, hsp-16.2, daf-2, and age-1 mutants, indicating dependency on these genetic pathways.	Drug Des Devel Ther. 2021 Oct 5;15:4177-4193
Wistar rats	Vascular dementia model induced by permanent bilateral common carotid artery ligation	Intravenous injection via tail vein	1, 3, 10 mg/kg	Once daily until the end of the experiment (day 56 post-surgery)	To evaluate the effect of pinocembrin on cognitive function in rats with vascular dementia. Results showed that pinocembrin significantly improved learning and memory deficits, reduced hippocampal neuronal damage, and upregulated the expression of proteins related to the Reelin-dab1 signaling pathway.	Drug Des Devel Ther. 2020 Sep 4;14:3577-3587.
Sprague-Dawley rats	Electrocoagulation-induced thrombotic focal ischemic rat model	Intravenous injection via tail vein	10 mg/kg	Single administration, observed for 24 hours	Pinocembrin significantly decreased the infarct volume, ameliorated t-PA-induced hemorrhagic transformation, and protected the blood-brain barrier. Metabolomics analysis revealed that pinocembrin had significant intervention effects on metabolites significantly altered after t-PA thrombolysis.	Acta Pharmacol Sin. 2021 Aug;42(8):1223-1234
C57BL/6J mice	Chronic unpredictable mild stress (CUMS) model	Oral gavage	10 mg/kg	Once daily for 3 weeks	Pinocembrin alleviated CUMS-induced depressive-like behaviors by ameliorating neuroinflammation and apoptosis.	Mol Med. 2020 May 27;26(1):53
Gallus gallus	Chick chorioallantoic membrane (CAM) model	Direct contact with vascularized region	10, 20, 65 μM	3 days	To evaluate the antiangiogenic activity of Pinocembrin in the chick chorioallantoic membrane model. The results showed that Pinocembrin significantly reduced the number of blood vessels.	Pharmaceutics. 2022 Feb 22;14(3):484.
C57BL/6 mice	Experimental autoimmune encephalomyelitis (EAE) model	Intraperitoneal injection	20 and 40 mg/kg	Daily, starting from the first sign of disease	Pinocembrin significantly ameliorated the disease severity of EAE, reduced the demyelination area and inflammatory cell infiltration.	Neurosci Bull. 2021 Sep;37(9):1314-1324
C57BL/6J mice	OVX-induced osteoporosis model	Intraperitoneal injection	20 mg/kg	Once daily for six weeks	Evaluate the therapeutic effect of PIN on osteoporosis induced by estrogen deficiency, showing significant reductions in serum TRAcP and CTX-1 levels and improvements in bone microstructure and biomechanical properties.	J Orthop Translat. 2024 Mar 27;45:197-210.
Kunming mice	Aβ25-35-induced Alzheimer's disease model	Oral	20 mg/kg, 40 mg/kg	Once daily for 8 days	To investigate the effect of pinocembrin on cognitive function and neuronal protection. Results showed that pinocembrin improved cognitive function, preserved the ultrastructural neuropil and decreased neurodegeneration of the cerebral cortex.	BMC Med. 2012 Sep 18;10:105.
C57BL/6 mice	Bleomycin-induced skin fibrosis model	Intradermal injection	20, 40, and 80 μM	Once daily for 3 weeks	To evaluate the effect of pinocembrin on bleomycin-induced skin fibrosis, results showed that pinocembrin significantly alleviated skin fibrosis	Biomolecules. 2021 Aug 19;11(8):1240.
C57BL/6J mice	Intermittent hypoxia (IH) model	Intraperitoneal injection	40 mg/kg	Every 2 days for 21 days	To evaluate the protective effects of Pinocembrin on intermittent hypoxia (IH)-induced neuroinflammation and cognitive dysfunction. Results showed that Pinocembrin significantly improved spatial learning and memory ability, reduced neuronal apoptosis and hippocampal inflammation, and enhanced BNIP3-mediated mitophagy.	J Neuroinflammation. 2020 Nov 11;17(1):337.
C57BL/6 mice	Collagenase-induced ICH model	Intravenous injection via tail vein	5 mg/kg	Starting at 2 h after ICH, twice daily until euthanasia	Pinocembrin dose-dependently reduced lesion volume (47.5% reduction at 5 mg/kg), ameliorated neurologic deficits, and reduced brain edema. Additionally, Pinocembrin suppressed microglial activation, decreased proinflammatory cytokines (TNF-α, IL-1β, and IL-6), and reduced the number of M1-like microglia.	Brain Behav Immun. 2017 Mar;61:326-339.
Sprague-Dawley rats	Post-infarct heart failure model	Intravenous injection	5 mg/kg	Every other day for 2 weeks	Pinocembrin improved cardiac function and remodeling by activating Nrf2/HO-1 signaling pathway, reducing fibrosis and apoptosis, and promoting angiogenesis	Mol Med. 2021 Sep 6;27(1):100.
Sprague-Dawley rats	Chronic ischaemic heart failure model	Tail vein injection	5 mg/kg	Daily for 2 months	Pinocembrin ameliorated arrhythmias in rats with chronic ischaemic heart failure, reduced the incidence and duration of ventricular fibrillation, and improved cardiac autonomic nerve remodeling.	Ann Med. 2021 Dec;53(1):830-840
Sprague-Dawley rats	Anxiety disorder model induced by empty bottle stimulation	Tail vein injection	5 mg/kg	Daily administration for the last 2 weeks	Pinocembrin significantly improved anxiety-like behaviors, alleviated electrophysiological and structural remodeling, and reduced AF susceptibility	Front Pharmacol. 2022 Oct 20;13:1004888

Bio Calculators
Preparing Stock Solutions		1mg	5mg	10mg
Preparing Stock Solutions	1 mM 5 mM 10 mM	3.90mL 0.78mL 0.39mL	19.51mL 3.90mL 1.95mL	39.02mL 7.80mL 3.90mL
Dissolving Methods	Animal experiment Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn: in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day; The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound. Protocol 1 Protocol 2

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CAS No.: 480-39-7

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CAS No.: 480-39-7

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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
Prevention
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