CAS No. :	548472-68-0
Formula :	C₃₀H₃₀Cl₂N₄O₄
M.W :	581.49
SMILES Code :	O=C1NCCN(C(N2[C@@H](C3=CC=C(Cl)C=C3)[C@@H](C4=CC=C(Cl)C=C4)N=C2C5=CC=C(OC)C=C5OC(C)C)=O)C1
Synonyms :	(±)-Nutlin-3
MDL No. :	MFCD07784509
InChI Key :	BDUHCSBCVGXTJM-UHFFFAOYSA-N
Pubchem ID :	216345

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

MOLM-13 cells	6 µM	0, 2, 4, 6, 8 hours	Nutlin-3 enhances p53 acetylation and increases levels of p53, MDM2, and p21	Mol Cancer. 2014 May 21;13:116.
PAEC	10 µM	24 hours	Nutlin-3 increased p53 and induced the formation of the PPARγ-p53 complex, assessed by immunoprecipitation with either anti-PPARγ or anti-p53 antibodies.	Circ Res. 2021 Feb 5;128(3):401-418.
293T cells	0.5mg/L	24 hours	Increased p53 transcriptional activity induced by Dox was partially dependent on PPARγ.	Circ Res. 2021 Feb 5;128(3):401-418.
MDA-MB 435S (breast cancer cells)	30 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis, leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
DLD-1 (colon cancer cells)	30 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis, leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
HeLa (cervical cancer cells)	30 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis, leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
T98G (glioblastoma cells)	30 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis, leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
RT4 schwannoma cells	0-10 µM	24, 48, 72 hours	Nutlin-3 inhibited the proliferation of schwannoma cells through a cooperative recovery of merlin and p53, accompanied by the shuttling of both proteins from the cytoplasm to the nucleus.	EBioMedicine. 2018 Oct;36:252-265.
HEI-193 schwannoma cells	0-10 µM	24, 48, 72 hours	Nutlin-3 combined with MG-132 significantly inhibited the growth of schwannoma cells through coordinated reactivation of p53.	EBioMedicine. 2018 Oct;36:252-265.
SAOS-2 cells	6 µM	4, 6 hours	Nutlin-3 enhances p53 acetylation in SAOS-2 cells, with acetylation levels higher than the increase in total p53 levels	Mol Cancer. 2014 May 21;13:116.
H1299 cells	6 µM	6 hours	Nutlin-3 significantly increases p53 acetylation levels in H1299 cells, with only a small increase in total p53 levels	Mol Cancer. 2014 May 21;13:116.
94T778 cells	10 µM	72 hours	Nutlin-3 treatment effectively stabilized p53 and upregulated direct p53 targets MDM2, p21, and PUMA. Under these conditions, most liposarcoma cells underwent cell-cycle arrest, with approximately 20% of cells undergoing apoptosis.	Cancer Res. 2023 Aug 1;83(15):2543-2556.
Lipo-246 cells	10 µM	72 hours	Nutlin-3 treatment effectively stabilized p53 and upregulated direct p53 targets MDM2, p21, and PUMA. Under these conditions, most liposarcoma cells underwent cell-cycle arrest, with approximately 20% of cells undergoing apoptosis.	Cancer Res. 2023 Aug 1;83(15):2543-2556.
Z-138	5 µM	8 hours	Nutlin-3 resulted in a reduction in cell proliferation/viability, an increase in the apoptotic fraction, and cell cycle arrest	Clin Cancer Res. 2009 Feb 1;15(3):933-42.
Granta 519	10 µM	8 hours	Nutlin-3 resulted in a reduction in cell proliferation/viability, an increase in the apoptotic fraction, and cell cycle arrest	Clin Cancer Res. 2009 Feb 1;15(3):933-42.
MINO	10 µM	8 hours	Nutlin-3 induced cell cycle arrest and reduced cell viability in the mutant TP53 MINO cells	Clin Cancer Res. 2009 Feb 1;15(3):933-42.
B-cell precursor acute lymphoblastic leukemia cells	0–10 µM		To evaluate the cytotoxic effect of nutlin-3 on ALL cells with different p53 status and MDM2 expression, it was found that ALL cells with wt-p53 are sensitive to nutlin-3, while ALL cells with p53-mutant or -null phenotype are not sensitive to nutlin-3	Leukemia. 2008 Apr;22(4):730-9.
Primary acute lymphoblastic leukemia cells	0–10 µM		To analyze the cytotoxic effect of nutlin-3 on primary ALL cells, it was found that primary ALL cells with wt-p53 are sensitive to nutlin-3, while primary ALL cells with p53 mutation are not sensitive to nutlin-3	Leukemia. 2008 Apr;22(4):730-9.
UKF-NB-3rNutlin10μM cells	10 µM		To study the effects of RITA on p53 activation and apoptosis, results showed RITA induced p53 activation and apoptosis	Cell Death Dis. 2012 Apr 5;3(4):e294.
BHK cells	10 µM	∼16 hours	Detection of p53-GFP ubiquitination and its inhibition by Nutlin-3	Nucleic Acids Res. 2022 Nov 28;50(21):e125.
SJSA-1 cells	10 µM	2-3 weeks	Test the long-term effect of Nutlin on SJSA-1 cells, results showed no colony formation	Oncogene. 2011 Nov 17;30(46):4678-86.
ARPE-19 cells	0.1–50 µM	24 and 48 hours	To evaluate the effects of Nutlin-3 on cell viability and proliferation. Results showed that Nutlin-3 significantly reduced cell viability and proliferation in a dose-dependent manner at both 24 and 48 hours.	Int J Nanomedicine. 2024 Apr 11;19:3513-3536.
PAEC cells	10 µM	24 hours	Nutlin-3 increases p53 levels and induces PPARγ-p53 complex formation	Circ Res. 2021 Feb 5;128(3):401-418.
HCT116 (colon cancer cells)	20 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
T98G (glioblastoma cells)	30 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
HeLa (cervical cancer cells)	30 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
DLD-1 (colon cancer cells)	30 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
MDA-MB 435S (breast cancer cells)	30 µM	24 hours	Nutlin-3 enhances the bortezomib sensitivity of p53-defective cancer cells by inducing paraptosis leading to cell death.	Exp Mol Med. 2017 Aug 11;49(8):e365.
A549-Atg5-null	10 µM	24 hours	To evaluate the effect of Nutlin-3 on PD-L1 expression, results showed PD-L1 expression was higher in Atg5-null cells	Cell Mol Biol Lett. 2020 Aug 31;25:41.
A549-Atg5-wt	10 µM	24 hours	To evaluate the effect of Nutlin-3 on PD-L1 expression, results showed PD-L1 expression was lower in Atg5-wt cells	Cell Mol Biol Lett. 2020 Aug 31;25:41.
A375 p53-null	10 µM	24 hours	To evaluate the effect of Nutlin-3 on cell surface expression of CD276 and PD-L1, results showed Nutlin-3 did not induce CD276 expression in p53-null cells	Cell Mol Biol Lett. 2020 Aug 31;25:41.
A375 p53-wt	10 µM	24 hours	To evaluate the effect of Nutlin-3 on cell surface expression of CD276 and PD-L1, results showed Nutlin-3 induced CD276 expression in a p53-dependent manner	Cell Mol Biol Lett. 2020 Aug 31;25:41.
HCT116 p53-null	10 µM	24 hours	To evaluate the effect of Nutlin-3 on cell surface expression of CD276 and PD-L1, results showed Nutlin-3 did not induce CD276 expression in p53-null cells	Cell Mol Biol Lett. 2020 Aug 31;25:41.
HCT116 p53-wt	10 µM	24 hours	To evaluate the effect of Nutlin-3 on cell surface expression of CD276 and PD-L1, results showed Nutlin-3 induced CD276 expression in a p53-dependent manner	Cell Mol Biol Lett. 2020 Aug 31;25:41.
OVCAR-3 ovarian cancer cells	20 µM	24 hours	OVCAR-3 cells harboring mutant p53 were not sensitized to rhTRAIL or D269H/E195R by nutlin-3, whereas cisplatin pre-treatment increased the apoptotic effect of both ligands.	Br J Cancer. 2013 Nov 12;109(10):2685-95.
Lovo colon cancer cells	5-20 µM	24 hours	Nutlin-3 dose-dependently enhanced p53, p21 and MDM2 levels, indicating transcriptional activation of p53 due to the effective disruption of the MDM2–p53 interaction. DR5 protein levels and membrane expression were also increased.	Br J Cancer. 2013 Nov 12;109(10):2685-95.
H460 non-small cell lung cancer cells	5-20 µM	24 hours	Nutlin-3 dose-dependently enhanced p53, p21 and MDM2 levels, indicating transcriptional activation of p53 due to the effective disruption of the MDM2–p53 interaction. DR5 protein levels and membrane expression were also increased.	Br J Cancer. 2013 Nov 12;109(10):2685-95.
A2780 ovarian cancer cells	5-20 µM	24 hours	Nutlin-3 dose-dependently enhanced p53, p21 and MDM2 levels, indicating transcriptional activation of p53 due to the effective disruption of the MDM2–p53 interaction. DR5 protein levels and membrane expression were also increased.	Br J Cancer. 2013 Nov 12;109(10):2685-95.
SJSA-1 cells	10 µM	3 days	Test the apoptosis-inducing effect of Nutlin on SJSA-1 cells, results showed ~40% of cells underwent apoptosis	Oncogene. 2011 Nov 17;30(46):4678-86.
SAOS-2 cells	6 µM	4 or 6 hours	To investigate the effect of Nutlin-3 on p53 acetylation, results showed Nutlin-3 enhanced p53 acetylation	Mol Cancer. 2014 May 21;13:116.
U-2 OS cells	5 µM	45 hours	Nutlin-3a in combination with actinomycin D significantly enhanced FASLG-induced apoptosis.	Apoptosis. 2024 Oct;29(9-10):1515-1528.
A549 cells	5 µM	45 hours	Nutlin-3a in combination with actinomycin D significantly enhanced FASLG-induced apoptosis, activating caspase-8, caspase-9, and caspase-3.	Apoptosis. 2024 Oct;29(9-10):1515-1528.
SMMC7721/As	20 µM	48 hours	Combination of Nutlin-3 and arsenic trioxide significantly inhibited proliferation and induced apoptosis in SMMC7721/As cells	Mol Cancer. 2014 May 31;13:133.
HepG2/As	20 µM	48 hours	Combination of Nutlin-3 and arsenic trioxide significantly inhibited proliferation and induced apoptosis in HepG2/As cells	Mol Cancer. 2014 May 31;13:133.
L02 cells	10 µM	48 hours	Nutlin-3 did not change IFI16 subcellular localization in L02 cells.	Acta Pharmacol Sin. 2015 Feb;36(2):252-8.
Hep3B cells	10 µM	48 hours	Nutlin-3 did not induce ectopic expression of IFI16 protein in Hep3B cells.	Acta Pharmacol Sin. 2015 Feb;36(2):252-8.
Huh-7 cells	10 µM	48 hours	Nutlin-3 did not induce ectopic expression of IFI16 protein in Huh-7 cells.	Acta Pharmacol Sin. 2015 Feb;36(2):252-8.
SMMC-7721 cells	10 µM	48 hours	Nutlin-3 significantly increased the expression levels of IFI16 and IFNB1 mRNA, and partially redistributed chromatin-bound IFI16 protein to the cytoplasm. These effects were blocked by pretreatment with pifithrin-α, a p53 inhibitor.	Acta Pharmacol Sin. 2015 Feb;36(2):252-8.
H1299 cells	6 µM	6 hours	To investigate the effect of Nutlin-3 on p53 acetylation, results showed Nutlin-3 enhanced p53 acetylation	Mol Cancer. 2014 May 21;13:116.
MOLM-13 cells	6 µM	6 hours	To investigate the effect of Nutlin-3 on p53 acetylation, results showed Nutlin-3 enhanced p53 acetylation	Mol Cancer. 2014 May 21;13:116.
UoCB6 cells	1–10 µM		Nutlin-3 treatment led to a substantial accumulation of the p53 protein as well as the expression of its direct targets p21, MDM2 and the pro-apoptotic BAX and PUMA proteins.	Leukemia. 2014 Mar;28(3):600-8.
REH cells	1–10 µM		Nutlin-3 treatment significantly reduced viability and increased apoptosis, while inducing p21 expression, leading to an increased proportion of cells in the G0/G1 phase.	Leukemia. 2014 Mar;28(3):600-8.
AT-2 cells	1–10 µM		Nutlin-3 treatment led to a substantial accumulation of the p53 protein as well as the expression of its direct targets p21, MDM2 and the pro-apoptotic BAX and PUMA proteins.	Leukemia. 2014 Mar;28(3):600-8.

Mice	EC-Bmpr2−/− mice	Intraperitoneal injection	12 mg/kg	Daily for two weeks	Nutlin-3a restored the PPARγ-p53 complex in EC-Bmpr2?/? mice, induced target gene expression, regenerated pulmonary microvessels, and reversed pulmonary hypertension.	Circ Res. 2021 Feb 5;128(3):401-418.
Nude mice	Orthotopic hepatic tumor model	Oral	200 mg/kg	Twice daily for 28 days	To evaluate the anti-tumor effect of Nutlin-3 combined with arsenic trioxide on orthotopic hepatic tumors in nude mice, results showed that the combination significantly inhibited tumor growth and lung metastasis.	Mol Cancer. 2014 May 31;13:133.
Mice	Lipo-246 xenograft model	Oral gavage	37.5 mg/kg	Days 1-5 of each week for up to 3 weeks	The combination of idasanutlin and carfilzomib significantly slowed tumor growth and improved survival.	Cancer Res. 2023 Aug 1;83(15):2543-2556.
BALB/c Nude mice	RT4 and HEI-193 schwannoma cell xenograft models	Intraperitoneal injection	40 mg/kg	Once daily for 14 days	Nutlin-3 combined with MG-132 significantly inhibited the growth of schwannoma xenografts and induced apoptosis in tumour cells.	EBioMedicine. 2018 Oct;36:252-265.

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

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CAS No.: 548472-68-0

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CAS No.: 548472-68-0

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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