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CAS No. :	499-44-5
Formula :	C₁₀H₁₂O₂
M.W :	164.20
SMILES Code :	O=C1C(O)=CC(C(C)C)=CC=C1
Synonyms :	β-Thujaplicin; NSC 18804; 4-Isopropyltropolone
MDL No. :	MFCD00040180
InChI Key :	FUWUEFKEXZQKKA-UHFFFAOYSA-N
Pubchem ID :	3611

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P264-P270-P301+P312+P330-P501

FPN1-deficient J774 macrophages	1 μM		Restored iron release in FPN1-deficient cells	Science. 2017 May 12;356(6338):608-616
PANC-1 human pancreatic cancer cells	80 μg/mL	10 h	To evaluate the effect of Hinokitiol on iron content and mitochondrial function in mammalian cells. Results showed that Hinokitiol had minor effects on iron content and mitochondrial function in mammalian cells, indicating selectivity towards fungal cells.	J Adv Res. 2021 Jun 17;34:65-77
BEAS-2B human bronchial epithelial cells	80 μg/mL	10 h	To evaluate the effect of Hinokitiol on iron content and mitochondrial function in mammalian cells. Results showed that Hinokitiol had minor effects on iron content and mitochondrial function in mammalian cells, indicating selectivity towards fungal cells.	J Adv Res. 2021 Jun 17;34:65-77
Candida albicans SC5314	2-8 μg/mL	30 min to 10 h	To evaluate the effect of Hinokitiol on fungal intracellular iron content and its inhibition of mitochondrial respiration. Results showed that Hinokitiol significantly reduced intracellular Fe2+ levels, inhibited the activities of mitochondrial respiratory chain complexes I and II, leading to decreased mitochondrial membrane potential and ATP production.	J Adv Res. 2021 Jun 17;34:65-77
Mfrn1-deficient MEL cells	1 μM		Restored iron uptake and hemoglobinization in Mfrn1-deficient cells	Science. 2017 May 12;356(6338):608-616
DS19 murine erythroleukemia (MEL) cells	1 μM	3 days	Restored iron uptake, iron-heme incorporation, and hemoglobinization in DMT1-deficient cells	Science. 2017 May 12;356(6338):608-616
Caco-2 gut epithelial cells	500 nM		Restored iron uptake and transepithelial iron transport in DMT1-deficient monolayers	Science. 2017 May 12;356(6338):608-616
Kupffer cells	5 μM	60 minutes	restore iron transport and reduce intracellular iron accumulation	Proc Natl Acad Sci U S A. 2022 Jun 28;119(26):e2121400119
RAW264.7 macrophages	5 μM		assess iron release and intracellular labile iron levels	Proc Natl Acad Sci U S A. 2022 Jun 28;119(26):e2121400119
HL-7702 cells	25, 50, 100, 200, 400 nM	24, 48, 72 hours	To evaluate the cytotoxicity of β-Thujaplicin on normal liver cells, results showed that β-Thujaplicin had minimal effect on the growth of HL-7702 cells	Cell Death Dis. 2019 Mar 15;10(4):255
HCCLM3 cells	25, 50, 100, 200, 400 nM	24, 48, 72 hours	To evaluate the cytotoxicity of β-Thujaplicin on HCC cells, results showed that β-Thujaplicin significantly inhibited the growth of HCCLM3 cells in a dose-dependent manner	Cell Death Dis. 2019 Mar 15;10(4):255
SMMC-7721 cells	25, 50, 100, 200, 400 nM	24, 48, 72 hours	To evaluate the cytotoxicity of β-Thujaplicin on HCC cells, results showed that β-Thujaplicin significantly inhibited the growth of SMMC-7721 cells in a dose-dependent manner	Cell Death Dis. 2019 Mar 15;10(4):255
HepG2 cells	25, 50, 100, 200, 400 nM	24, 48, 72 hours	To evaluate the cytotoxicity of β-Thujaplicin on HCC cells, results showed that β-Thujaplicin significantly inhibited the growth of HepG2 cells in a dose-dependent manner	Cell Death Dis. 2019 Mar 15;10(4):255
CRL-8024 cells	10–100μM		To evaluate the effect of hinokitiol on HCC cell proliferation, results showed that hinokitiol significantly attenuated the proliferation of HCC cell lines in a dose-dependent manner while downregulating the protein levels of UHRF1, GLI1, CD44, and CD133.	Cell Death Dis. 2023 Jun 28;14(6):381
MEL cells	1 μM		probe hemoglobinization and iron uptake	Proc Natl Acad Sci U S A. 2022 Jun 28;119(26):e2121400119
MDA-MB-231 cells	6.25 to 100 µg/mL	48 hours	To evaluate anticancer efficacy, results showed that Hinokitiol-loaded phytosomal formulation had higher cytotoxicity than pure Hinokitiol, with an IC50 value of 5.7 µg/mL	Int J Nanomedicine. 2024 Oct 12;19:10321-10339
MCF-7 cells	6.25 to 100 µg/mL	48 hours	To evaluate anticancer efficacy, results showed that Hinokitiol-loaded phytosomal formulation had higher cytotoxicity than pure Hinokitiol, with an IC50 value of 18.6 µg/mL	Int J Nanomedicine. 2024 Oct 12;19:10321-10339
normal liver cell line HL-7702	25, 50, 100, 200, 400 nM	24, 48, 72 h	To evaluate the effect of β-Thujaplicin on normal liver cells, results showed that β-Thujaplicin had only a slight effect on the viability of HL-7702 cells at 400 nM	Cell Death Dis. 2019 Mar 15;10(4):255.
human hepatoma cell lines HCCLM3	25, 50, 100, 200, 400 nM	24, 48, 72 h	To evaluate the inhibitory effect of β-Thujaplicin on HCC cell growth, results showed that β-Thujaplicin significantly inhibited the viability of HCCLM3 cells in a dose-dependent manner	Cell Death Dis. 2019 Mar 15;10(4):255.
human hepatoma cell lines SMMC-7721	25, 50, 100, 200, 400 nM	24, 48, 72 h	To evaluate the inhibitory effect of β-Thujaplicin on HCC cell growth, results showed that β-Thujaplicin significantly inhibited the viability of SMMC-7721 cells in a dose-dependent manner	Cell Death Dis. 2019 Mar 15;10(4):255.
human hepatoma cell lines HepG2	25, 50, 100, 200, 400 nM	24, 48, 72 h	To evaluate the inhibitory effect of β-Thujaplicin on HCC cell growth, results showed that β-Thujaplicin significantly inhibited the viability of HepG2, SMMC-7721, and HCCLM3 cells in a dose-dependent manner	Cell Death Dis. 2019 Mar 15;10(4):255.

Galleria mellonella	Candida albicans-infected larvae	Injection	2 μg/larva	Single dose, observed for 7 days	To evaluate the therapeutic effect of Hinokitiol on Candida albicans infection in vivo. Results showed that Hinokitiol significantly improved the survival rate of infected larvae and reduced fungal burden.	J Adv Res. 2021 Jun 17;34:65-77
Belgrade rats	DMT1-deficient rat model	Oral gavage	1.5 mg/kg	Single dose	Promoted gut iron absorption in DMT1-deficient rats	Science. 2017 May 12;356(6338):608-616
Nude mice	HepG2 tumor xenograft model	Intraperitoneal injection	5 mg/kg body weight	Once daily for 15 days	To evaluate the inhibitory effect of β-Thujaplicin on HepG2 tumor growth in vivo, results showed that β-Thujaplicin significantly reduced tumor volume and weight	Cell Death Dis. 2019 Mar 15;10(4):255
Mice	Myc-driven HCC model	Intraperitoneal injection	25 mg/kg	Twice a week from 4 to 9 weeks of birth	To evaluate the effect of hinokitiol on Myc-driven HCC mouse model, results showed that hinokitiol significantly reduced tumor growth and CSC phenotypes, and downregulated the expression of UHRF1, GLI1, CD44, and CD133.	Cell Death Dis. 2023 Jun 28;14(6):381
Mice	FPN1-deficient mice	Intraperitoneal injection	10 mg/kg	Daily for 1 week	Restore hemoglobinization and iron distribution	Proc Natl Acad Sci U S A. 2022 Jun 28;119(26):e2121400119
Nude mice	HepG2 tumor xenograft model	Intraperitoneal injection	5 mg/kg body weight	Once daily for 15 days	To verify the antitumor effect of β-Thujaplicin in vivo, results showed that β-Thujaplicin significantly inhibited the growth of HepG2 tumor xenografts	Cell Death Dis. 2019 Mar 15;10(4):255.

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CAS No.: 499-44-5

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CAS No.: 499-44-5

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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