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CAS No. :	138-59-0
Formula :	C₇H₁₀O₅
M.W :	174.15
SMILES Code :	O[C@H]1[C@H](O)[C@H](O)C=C(C(O)=O)C1
Synonyms :	NSC 59257; Shikimate; (–)-Shikimic Acid, L-Shikimic Acid, Shikimic acid
MDL No. :	MFCD00066278
InChI Key :	JXOHGGNKMLTUBP-HSUXUTPPSA-N
Pubchem ID :	8742

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

3T3-L1 cells	0, 10, 20, 40, 80, 160 µM	24 hours	Evaluate the cytotoxicity of shikimic acid in 3T3-L1 cells, showing cell viability remained above 70% at 160 μM concentration.	Int J Mol Sci. 2019 Jan 29;20(3):582
Huh7 cells	0, 10, 20, 40, 80, 160 µM	24 hours	Evaluate the cytotoxicity of shikimic acid in Huh7 cells, showing cell viability remained above 70% at 160 μM concentration.	Int J Mol Sci. 2019 Jan 29;20(3):582
HepG2 cells	0, 10, 20, 40, 80, 160 µM	24 hours	Evaluate the cytotoxicity of shikimic acid in HepG2 cells, showing cell viability remained above 70% at 160 μM concentration.	Int J Mol Sci. 2019 Jan 29;20(3):582
BV2 cells	5 µM and 10 µM	24 hours	SA inhibited the production of NO and ROS in LPS-stimulated BV2 cells	Front Pharmacol. 2023 Nov 2;14:1265571
SW1353 human chondrocytes	10 mM	24 hours	To evaluate the effects of SA on IL-1β-induced inflammatory response and cartilage degradation. SA significantly alleviated the IL-1β-induced increases in iNOS, COX-2, MMP3, MMP13, ADAMTS5, and type X collagen expression and restored type II collagen expression.	Front Pharmacol. 2021 Jul 27;12:634822
HL-1 cells	250 µM to 31.25 µM	24 hours	Promoted proliferation of normal HL-1 cells by an average of 31.0%	Pharmaceuticals (Basel). 2024 Nov 5;17(11):1485
LLC-PK1 cells	25 and 50 µM	24 hours	To evaluate the protective effect of shikimic acid against cisplatin-induced renal cell damage. Results showed that shikimic acid reversed the decrease in cell viability induced by cisplatin and reduced oxidative stress and apoptosis.	Plants (Basel). 2020 Dec 1;9(12):1681
Human dermal fibroblasts (HDFs)	25 mM	24 hours	To evaluate the protective effect of shikimic acid against UV-induced cellular senescence, results showed that shikimic acid reduced the levels of H4K16ac and H3K9ac by activating SIRT1, thereby inhibiting cellular senescence.	Aging (Albany NY). 2021 Apr 26;13(9):12308-12333
HL-1 cells	250 µM to 31.25 µM	3 hours	Enhanced survival rate of HL-1 cells exposed to heat stress by approximately 59.9%, downregulated expression of Hsp90 and Hsp70	Pharmaceuticals (Basel). 2024 Nov 5;17(11):1485
Duck myofibrillar protein	1:50,000, 1:25,000, 1:12,500, 1:6250 (g/g)	30 minutes	To study the effect of shikimic acid on the oxidation and structure of duck myofibrillar protein. Results showed that shikimic acid significantly reduced protein oxidation and improved thermal stability.	Foods. 2024 Oct 21;13(20):3338
Primary rat chondrocytes	10 mM	48 hours	To evaluate the effects of SA on IL-1β-induced chondrocyte degeneration. SA significantly attenuated IL-1β-associated degeneration and matrix disruption.	Front Pharmacol. 2021 Jul 27;12:634822

C57BL/6J mice	DSS-induced ulcerative colitis model	Intragastric administration	10, 30, 50 mg/kg	Once daily for 8 days	To evaluate the therapeutic effects of SA on DSS-induced colitis, results showed SA slowed weight loss, reduced DAI score, enhanced intestinal barrier function, reduced colonic structure destruction, inhibited phosphorylation of key proteins in MAPK and NF-κB signaling pathways, inhibited expression of inflammatory factors TNF-α, IL-1β, and MPO, decreased IFN-γ expression, and increased IgG content. Additionally, 50 mg/kg SA treatment increased Bacteroidetes and decreased Proteobacteria in cecal feces of colitis mice and increased gut species richness.	J Agric Food Chem. 2023 Jun 14;71(23):8906-8914
C57/BL6 mice	LPS-induced neuroinflammation model	Intraperitoneal injection	100 mg/kg	Once daily for 4 weeks	SA ameliorated the neurological damage and behavioral deficits caused by LPS injection in mice	Front Pharmacol. 2023 Nov 2;14:1265571
Rats	Sprague Dawley rats	Intravenous and intragastric	2 mg/kg iv, 100 mg/kg ig	Single dose	To study the pharmacokinetic behavior of shikimic acid in rats. After iv administration, shikimic acid exhibited bi-exponential decay with rapid distribution (5.57 h?1) up to 1 h followed by slow elimination (0.78 h?1). After ig administration, the plasma shikimic acid level peaked at about 3 h and then declined mono-exponentially (half-life =1.3 h). The absolute oral bioavailability was about 10%.	Pharmaceutics. 2020 Aug 29;12(9):824
Sprague Dawley rats	ACLT-induced osteoarthritis model	Intra-articular injection	20 mM	Twice a week for one month	To evaluate the effects of SA on the progression of osteoarthritis. SA treatment alleviated the progression of OA, as evidenced by reduced articular cartilage erosion and loss of safranin O staining and toluidine blue staining.	Front Pharmacol. 2021 Jul 27;12:634822
BALB/c mice	Cisplatin-induced acute kidney injury model	Oral	25 and 50 mg/kg	Once daily for 4 days	To assess the protective effect of shikimic acid against cisplatin-induced kidney injury. Results showed that shikimic acid reduced serum creatinine levels and improved histological kidney injury.	Plants (Basel). 2020 Dec 1;9(12):1681
Growing pigs	Healthy growing pigs	Intragastric and intravenous	50 mg/kg (intragastric), 2 mg/kg (intravenous)	Single dose, observed for 24 hours	To study the pharmacokinetics of shikimic acid in pigs and its impact on humoral immunity. Results showed rapid absorption after intragastric administration, with a plasma Cmax of 10,823.44 ng/mL and t1/2 of 1.81 h. Intravenous administration followed a two-compartment open model with t1/2 of 3.66 h. Absolute bioavailability was 21.68%. SA plasma concentration showed strong positive correlation with changes in C3, C4, IgG, IgA, and IgM (0.6 < R < 1, P < 0.0001).	J Agric Food Chem. 2024 Nov 27;72(47):26224-26235
Growing pigs	Healthy growing pigs	Intragastric and intravenous administration	50 mg/kg (intragastric), 2 mg/kg (intravenous)	Single dose, observed for 24 hours	To study the pharmacokinetics of shikimic acid in pigs and its impact on humoral immunity. Results showed that SA was rapidly absorbed after intragastric administration, with a plasma Cmax of 10,823.44 ng/mL and t1/2 of 1.81 h; intravenous administration followed a two-compartment open model with t1/2 of 3.66 h. The absolute bioavailability was 21.68%. Additionally, SA concentration showed a strong positive correlation with changes in C3, C4, IgG, IgA, and IgM (0.6 < R < 1, P < 0.0001).	J Agric Food Chem. 2024 Nov 27;72(47):26224-26235
Tomato (Solanum lycopersicum L.)	Tomato plants	Seed soaking	60 ppm	Single treatment, lasting the entire growing season	To study the effects of shikimic acid on the growth, yield, and fruit quality of tomato under cold stress. Results showed that shikimic acid treatment improved plant growth parameters, yield, and fruit quality.	Plants (Basel). 2022 Oct 24;11(21):2822

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CAS No.: 138-59-0

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CAS No.: 138-59-0

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Product Details of Shikimic acid

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Precautionary Statements-General

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Preparing Stock Solutions		1mg	5mg	10mg
Preparing Stock Solutions	1 mM 5 mM 10 mM	5.74mL 1.15mL 0.57mL	28.71mL 5.74mL 2.87mL	57.42mL 11.48mL 5.74mL
Dissolving Methods	Animal experiment The prepared working fluid is recommended to be prepared now and used up as soon as possible in a short period of time. 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

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