Name: AKBA | Acetyl-11-keto-β-boswellic acid; 3-O-acetyl-11-keto-β-Boswellic acid
Brand: Ambeed
SKU: A106831
Rating: 4.0 (99 reviews)

CAS No. :	67416-61-9
Formula :	C₃₂H₄₈O₅
M.W :	512.72
SMILES Code :	C[C@@]([C@@](C1=C2)(CC[C@@](C)(CC[C@H]3C)[C@@]1([H])[C@H]3C)C)(CC[C@@]4([H])[C@@]5(C)C(O)=O)[C@@](C2=O)([H])[C@]4(CC[C@H]5OC(C)=O)C
Synonyms :	Acetyl-11-keto-β-boswellic acid; 3-O-acetyl-11-keto-β-Boswellic acid; Acetylketo-β-boswellic acid
MDL No. :	MFCD03788777
InChI Key :	HMMGKOVEOFBCAU-BCDBGHSCSA-N
Pubchem ID :	11168203

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Mouse primary keratinocytes	20 μM	12 h	AKBA decreases H3K27me3 methylation level	EBioMedicine. 2019 Jan;39:575-590
HaCaT cells	20 μM	12 h	AKBA inhibits MAT2A function, decreases SAM level and SAM/SAH ratio	EBioMedicine. 2019 Jan;39:575-590
U87-MG cells	10 mM, 20 mM, 30 mM	24 h	To detect the inhibitory effect of AKBA on autophagy in U87-MG cells using transmission electron microscopy. Results showed that AKBA significantly inhibited autophagy in U87 cells.	Acta Pharm Sin B. 2020 Feb;10(2):301-312
HEK293 cells	25 μM	180 min	AKBA significantly increased the formation of 15-LOX products in cells expressing 15-LOX-1 and 15-LOX-2.	Adv Sci (Weinh). 2023 Feb;10(6):e2205604
M2-MDMs	10 μM	180 min	AKBA significantly increased the formation of 12/15-LOX-derived lipid mediators and SPMs, particularly in M2-MDMs.	Adv Sci (Weinh). 2023 Feb;10(6):e2205604
Human monocytes	10 μM	90 min	AKBA significantly elevated the levels of 15-LOX and 12-LOX products and increased the formation of SPMs, especially in M2-MDMs.	Adv Sci (Weinh). 2023 Feb;10(6):e2205604
M1-like macrophages	10 μM	90 min	AKBA significantly reduced the formation of LTB4 while increasing the production of 12-HETE.	Nat Chem Biol. 2020 Jul;16(7):783-790
Neutrophils	10 μM	90 min	AKBA significantly reduced the levels of 5-HETE and LTB4 while increasing the production of 12-HETE.	Nat Chem Biol. 2020 Jul;16(7):783-790
HEK293 cells	25 μM	15 min	AKBA significantly reduced the formation of 5-LOX products (e.g., 5-HETE and LTB4) while increasing the production of 12-HETE.	Nat Chem Biol. 2020 Jul;16(7):783-790
Human prostate cancer cells (PC-3)	50μM		AKBA inhibited PC-3 cell proliferation, requiring a higher concentration than that needed to suppress endothelial cell proliferation.	Cancer Res. 2009 Jul 15;69(14):5893-900
Human umbilical vascular endothelial cells (HUVECs)	5-10 μM	6-8 h	AKBA significantly suppressed or terminated VEGF-induced tubular formation of endothelial cells.	Cancer Res. 2009 Jul 15;69(14):5893-900
Human umbilical vascular endothelial cells (HUVECs)	1-5 μM	24 h	AKBA inhibited VEGF-induced HUVEC migration and invasion in a dose-dependent manner.	Cancer Res. 2009 Jul 15;69(14):5893-900
U87-MG human glioblastoma cells	10, 20, 30 μM	24 and 48 h	AKBA inhibited cell proliferation, caused the release of LDH, decreased DNA synthesis, and inhibited the migration, invasion, and colony formation of U87-MG human glioblastoma cells.	J Exp Clin Cancer Res. 2018 Jul 3;37(1):132
U251 human glioblastoma cells	10, 20, 30 μM	24 and 48 h	AKBA inhibited cell proliferation, caused the release of LDH, decreased DNA synthesis, and inhibited the migration, invasion, and colony formation of U251 human glioblastoma cells.	J Exp Clin Cancer Res. 2018 Jul 3;37(1):132
PC3 cells	5, 10, 20, 30, 40 μM	48 h	AKBA dose-dependently inhibited cell proliferation in PC3 cells, with an IC50 value of approximately 21μM.	Acta Pharmacol Sin. 2019 May;40(5):689-698
PC3/Doc cells	5, 10, 20, 30, 40 μM	48 h	AKBA dose-dependently inhibited cell proliferation and induced cell apoptosis in docetaxel-resistant PC3/Doc cells, with an IC50 value of approximately 17μM in anti-proliferation.	Acta Pharmacol Sin. 2019 May;40(5):689-698
LS174T cells	20 μM	72 h	AKBA inhibited growth of LS174T cells, resulting in a 40-50% reduction in cell numbers.	Br J Pharmacol. 2006 Aug;148(8):1099-107
HT-29 cells	30 μM	72 h	AKBA inhibited growth of HT-29 cells, resulting in a 40-50% reduction in cell numbers.	Br J Pharmacol. 2006 Aug;148(8):1099-107
HCT-116 cells	5-25 μM	24-72 h	AKBA inhibited cellular growth in a time- and dose-dependent manner in HCT-116 cells, leading to G1 phase cell cycle arrest accompanied by downregulation of cyclin D1, E, CDK2, CDK4, and phosphorylated Rb, and upregulation of p21 expression.	Br J Pharmacol. 2006 Aug;148(8):1099-107
Schwann cells	2 µg/mL	0, 6, 12, 24 h	AKBA treatment significantly increased p-ERK1/2 expression in a time-dependent manner.	Neural Regen Res. 2018 Mar;13(3):484-491
Schwann cells	1.25, 2.5, 5, 10, 20 µg/mL	24 h	AKBA significantly promoted SC proliferation at concentrations of 1.25–5 µg/mL, peaking at 2 µg/mL; inhibited proliferation at >5 µg/mL.	Neural Regen Res. 2018 Mar;13(3):484-491

BALB/c nude mice	Orthotopic U87-MG glioblastoma model	Oral administration	100 mg/kg, 200 mg/kg	Once daily for 21 days	To evaluate the anti-tumor effects of AKBA on orthotopic glioblastoma. MRI results showed that AKBA significantly inhibited tumor growth without obvious weight loss or abnormal behavior.	Acta Pharm Sin B. 2020 Feb;10(2):301-312
BALB/c-nu nude mice	U87-MG human glioblastoma xenograft model	Oral	100 mg/kg	Once daily for 14 days	Oral administration of AKBA significantly suppressed the tumorigenicity of U87-MG cells in a xenograft mouse model.	J Exp Clin Cancer Res. 2018 Jul 3;37(1):132
C57BL/6 mice	RM-1/Doc homograft model	Intraperitoneal injection	30 mg/kg	Once daily for 14 days	AKBA significantly suppressed the growth of RM-1/Doc homografts without decreasing body weight.	Acta Pharmacol Sin. 2019 May;40(5):689-698
BALB/cA nude mice	Human prostate tumor xenograft model	Subcutaneous injection	10 mg/kg	Once daily for 30 days	AKBA significantly suppressed tumor volume and weight growth and inhibited tumor angiogenesis.	Cancer Res. 2009 Jul 15;69(14):5893-900
Sprague-Dawley rats	Sciatic nerve injury model	Intraperitoneal injection	1.5, 3, 6 mg/kg	Once every 2 days for 30 days	3 and 6 mg/kg AKBA significantly increased sciatic nerve index, Cuadros index of triceps muscle, p-ERK1/2 expression, and S100 immunoreactivity.	Neural Regen Res. 2018 Mar;13(3):484-491
Mice	Zymosan-induced peritonitis	Intraperitoneal injection	20 mg/kg	Single dose, lasting 24 hours	AKBA significantly elevated SPM levels and promoted the resolution of inflammation.	Adv Sci (Weinh). 2023 Feb;10(6):e2205604

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
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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CAS No.: 67416-61-9

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CAS No.: 67416-61-9

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