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CAS No. :	471-05-6
Formula :	C₁₅H₂₂O
M.W :	218.33
SMILES Code :	CC(/C=C/1)(C)C/C=C(C)/CC/C=C(C)/C1=O
MDL No. :	MFCD03700769

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H319-H372-H410
Precautionary Statements:	P273-P301+P312+P330-P305+P351+P338-P314
Class:	9
UN#:	3077
Packing Group:	Ⅲ

Huh7	50 µM	24 and 48 hours	Induced cell cycle arrest and apoptosis	Mol Cancer Res. 2018 Feb;16(2):256-268
MHCC-LM3	50 µM	24 hours	Inhibited PI3K/AKT/mTOR and STAT3 signaling pathways	Mol Cancer Res. 2018 Feb;16(2):256-268
Murine bone marrow-derived macrophages	10-50 µM	1 hour pretreatment followed by LPS or LPS/ATP treatment	Suppressed the production of IL-6, TNF-α, and IL-1β	Front Pharmacol. 2021 May 11;12:652860
J774A.1 cells	20 and 40 µM	1 hour pretreatment followed by LPS treatment for 2 hours	Inhibited the phosphorylation of ERK, did not affect the phosphorylation of JNK and p38 MAPK	Front Pharmacol. 2021 May 11;12:652860
Murine peritoneal macrophages	10-50 µM	1 hour pretreatment followed by LPS treatment for 24 hours	Inhibited the production of NO and IL-6, varied effects on TNF-α depending on concentration	Front Pharmacol. 2021 May 11;12:652860
J774A.1 cells	10-50 µM	1 hour pretreatment followed by LPS treatment for 24 hours	Suppressed the production of IL-6, increased TNF-α production at high doses	Front Pharmacol. 2021 May 11;12:652860
J774A.1 cells	10-50 µM	1 hour pretreatment followed by LPS treatment for 24 hours	Inhibited the production of NO, IL-6, and PGE2, suppressed the expression of iNOS and COX-2	Front Pharmacol. 2021 May 11;12:652860
J774A.1 cells	0-50 µM	1 hour pretreatment followed by LPS/ATP or LPS/nigericin treatment	Suppressed the secretion of IL-1β, inhibited the activation of NLRP3 inflammasome	Front Pharmacol. 2021 May 11;12:652860
Human neuroblastoma SH-SY5Y cells	1 µM	24 hours	To investigate the effect of MSC on apoptosis in Clu-knockdown SH-SY5Y cells. Results showed that 1 μM MSC could reverse the decrease in antioxidative capacity, Bcl-2/Bax ratio, and increase in caspase-8 activity caused by Clu-knockdown, thereby inhibiting apoptosis and maintaining cell viability.	Invest New Drugs. 2022 Apr;40(2):224-231
Mouse neuroblastoma N2a cells	1 µM	24 hours	To investigate the effect of MSC on apoptosis in Clu-knockdown N2a cells. Results showed that 1 μM MSC could reverse the decrease in antioxidative capacity, Bcl-2/Bax ratio, and increase in caspase-8 activity caused by Clu-knockdown, thereby inhibiting apoptosis and maintaining cell viability.	Invest New Drugs. 2022 Apr;40(2):224-231
Primary microglial cells	1, 3, or 10 μg/ml	24 hours	Zerumbone significantly reduced the production of IL-1β and TNF-α while increasing IL-10 production, and dose-dependently increased the mRNA levels of CD206, IL-10, and ARG-1, demonstrating its anti-inflammatory effects and ability to promote an anti-inflammatory phenotype in primary microglial cells.	J Neuroinflammation. 2020 Feb 17;17(1):61
N9 microglial cell line	1, 3, or 10 μg/ml	24 hours	Zerumbone significantly suppressed NO production and dose-dependently decreased the mRNA levels of IL-1β, IL-6, iNOS, and TNF-α, while increasing the mRNA levels of CD206, IL-10, and ARG-1, indicating its anti-inflammatory effects and ability to promote a switch in microglial phenotype from pro-inflammatory to anti-inflammatory.	J Neuroinflammation. 2020 Feb 17;17(1):61
U87MG cells	10-50 µM	24 hours	Zerumbone decreased the viability of U87MG cells in a dose-dependent manner.	J Biomed Sci. 2012 Oct 5;19(1):86
GBM8401 cells	10-50 µM	24 hours	Zerumbone induced apoptosis in GBM8401 cells in a dose-dependent manner, confirmed by MTT assay and flow cytometry.	J Biomed Sci. 2012 Oct 5;19(1):86
SH-SY5Y neuroblastoma cells	8 mg/ml	24 hours	To investigate the effect of Zerumbone on the expression of α2A-adrenergic, TRPV1, and NMDA NR2B receptors in LPS-induced SH-SY5Y neuroblastoma cells. Results showed that Zerumbone significantly increased the expression of α2A-adrenergic receptors while down-regulating TRPV1 and NMDA NR2B receptors.	Front Pharmacol. 2020 Mar 4;11:92
HCT116 colon cancer cells	5, 10, 20 µM	24 hours	To investigate the inhibitory effect of Zerumbone on the proliferation of HCT116 cells and its association with TNF-α. Results showed that with increasing concentration of Zerumbone, there was a reduction in HCT116 cell proliferation and higher TNF-α inhibition.	Sci Rep. 2018 Mar 6;8(1):4090
L929 cells	30.5 ± 1.5 µM (IC50)	24 hours	To assess the toxicity of Zerumbone on normal L929 cells, results showed lower toxicity in normal cells.	Cell Prolif. 2019 Mar;52(2):e12558
HeLa cells	14.2 ± 0.5 µM (IC50)	24 hours	To evaluate the inhibitory effect of Zerumbone on HeLa cell proliferation, results showed selective inhibition through enhanced cellular uptake.	Cell Prolif. 2019 Mar;52(2):e12558
FaDu cells	10, 30, 100 µM	24 hours (apoptosis assay), 48 hours (qPCR, Western blot, ELISA analyses), 14 days (plate clone formation assay)	Tilianin inhibited FaDu cell proliferation and induced apoptosis in a dose-dependent manner. It upregulated pro-apoptotic factors Bax and Bad, downregulated anti-apoptotic factors Bcl-2 and Bcl-xL, activated caspase-3 and PARP, and stimulated cytochrome c release, thereby inducing apoptosis via the mitochondrion-dependent intrinsic apoptotic pathway.	Nutrients. 2022 Dec 19;14(24):5402
Helicobacter pylori 60190	6.25, 12.5, 25, 50, 100 µM	3 days	Determine the minimal inhibitory concentration (MIC) of Zerumbone, which was 50 µM in agar dilution and 100 µM in broth dilution	Molecules. 2021 May 1;26(9):2663
HT29/C1 cells	6.25 µM	3 hours	Suppressed BFT-induced NF-κB signaling and IL-8 secretion but did not affect E-cadherin cleavage.	Int J Mol Sci. 2019 Sep 14;20(18):4560
Candida albicans (CaR)	128 µg/mL	5, 10, 20 min	To assess the effect of Zerumbone on fluconazole-resistant Candida albicans biofilms. Results showed that ZER at 128 µg/mL reduced cellular viability by approximately 36.99% and decreased insoluble biomass (13%), proteins (18%), water-soluble polysaccharides (65%), alkali-soluble polysaccharides (10%), and extracellular DNA (23%) in CaR biofilms.	J Fungi (Basel). 2023 May 16;9(5):576
Candida albicans (CaS)	256 µg/mL	5, 10, 20 min	To assess the effect of Zerumbone on fluconazole-susceptible Candida albicans biofilms. Results showed that ZER at 256 µg/mL reduced cellular viability by approximately 38.51% and decreased total biomass (57%), insoluble biomass (45%), water-soluble polysaccharides (65%), proteins (18%), and extracellular DNA (78%) in CaS biofilms.	J Fungi (Basel). 2023 May 16;9(5):576
RAW 264.7 cells	2.5~20 µM	6 hours	Zerumbone inhibited iNOS and COX-2 protein expressions and reduced NO and PGE2 production, while inducing HO-1 expression.	Int J Mol Sci. 2016 Feb 18;17(2):249
HepG2	14 µM	72 hours	Inhibited HCC cell proliferation by G2/M phase arrest and inducing apoptosis	Mol Cancer Res. 2018 Feb;16(2):256-268

ICR mice	Chronic constriction injury (CCI)-induced neuropathic pain model	Intraperitoneal injection	10 mg/kg	Single administration, behavioral tests conducted 30 minutes after administration	To investigate the anti-allodynic and antihyperalgesic effects of Zerumbone in the CCI-induced neuropathic pain model and its mechanisms. Results showed that Zerumbone exerted anti-neuropathic effects by modulating α1-, α2-, β1-, and β2-adrenoceptors as well as TRPV1 and NMDA NR2B receptors.	Front Pharmacol. 2020 Mar 4;11:92
ICR mice	Chronic constriction injury (CCI)-induced neuropathic pain model	Intraperitoneal injection	10 mg/kg	Single administration, behavioral tests conducted 30 minutes post-administration	To elucidate the mechanisms underlying zerumbone’s antineuropathic actions via cannabinoid and PPAR receptors. Results showed that zerumbone exerts anti-allodynic and antihyperalgesic effects against mechanical allodynia and thermal hyperalgesia through CB1, PPARα, and PPARγ receptors.	Molecules. 2021 Jun 24;26(13):3849
Male ICR mice	Chronic constriction injury (CCI)-induced neuropathic pain model	Intraperitoneal injection	10 mg/kg	Single administration, tests performed 30 minutes post-administration	To investigate the analgesic effects of Zerumbone via potassium channels and opioid receptors in CCI-induced neuropathic pain. Results showed that Zerumbone significantly alleviated mechanical allodynia and thermal hyperalgesia.	Molecules. 2020 Aug 26;25(17):3880
ICR mice	Acetic acid-induced writhing response model	Intraperitoneal injection	10 or 50 mg/kg	Single dose	Zerumbone significantly reduced the number of acetic acid-induced writhing responses.	Int J Mol Sci. 2016 Feb 18;17(2):249
Male albino mice	ZEA-induced hepatotoxicity model	Oral gavage	15 mg/kg	Once daily for 4 weeks	ZER exhibited a protective effect against ZEA-induced toxicity by ameliorating inflammation and oxidative stress-induced apoptosis. ZER decreased the levels of alkaline phosphatase and alanine aminotransferase (ALT) in serum and attenuated the inflammatory response by significantly reducing the levels of pro-inflammatory factors, including IL-1β, IL-6, and TNF-α. Additionally, ZER reduced the hepatic malondialdehyde (MDA) concentration and increased the activities of superoxide dismutase (SOD), glutathione (GSH), and catalase (CAT). ZER also alleviated ZEA-induced apoptosis by regulating the PI3K/AKT pathway and the expression of Nrf2 and HO-1.	Antioxidants (Basel). 2021 Oct 12;10(10):1593
NSG mice	Subcutaneous and orthotopic HCC xenograft models	Intraperitoneal injection	20 mg/kg/day	Once daily for 3 weeks	Suppressed HCC xenograft growth and lung metastasis	Mol Cancer Res. 2018 Feb;16(2):256-268
APP/PS1 transgenic mice	Alzheimer's disease model	Oral gavage	25 mg/kg	Once daily for 20 days	Zerumbone significantly ameliorated deficits in both non-cognitive and cognitive behaviors in transgenic APP/PS1 mice, reduced β-amyloid deposition, attenuated pro-inflammatory microglial activation in the cortex and hippocampus, and increased the proportion of anti-inflammatory microglia. Additionally, zerumbone downregulated the expression of key MAPK pathway molecules such as p38 and ERK.	J Neuroinflammation. 2020 Feb 17;17(1):61
Wistar albino rats	Collagen-induced arthritis (CIA) model	Oral	25 mg/kg and 50 mg/kg	Once daily for 20 days	To evaluate the therapeutic effects of Zerumbone on collagen-induced arthritis. Results showed that Zerumbone significantly reduced the clinical severity of arthritis, decreased oxidative stress and inflammatory cytokine levels, and restored normal histology in joints and tissues.	ACS Omega. 2023 Jan 10;8(3):2982-2991
C57BL/6 mice	ETBF infection-induced colitis model	Oral	30 or 60 mg/kg	Once daily for 7 days	Zerumbone reduced ETBF-induced colonic inflammation, prevented weight loss and splenomegaly, reduced colonic inflammation with decreased macrophage infiltration, and decreased expression of IL-17A, TNF-α, KC, and iNOS, while inhibiting NF-κB signaling.	Int J Mol Sci. 2019 Sep 14;20(18):4560

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CAS No.: 471-05-6

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CAS No.: 471-05-6

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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