Shikimic acid

Shikimic acid - Names and Identifiers

Name	Shikimic acid
Synonyms	Shikimicacid Shikimic acid L-SHIKIMIC ACID (-)-Shikimic acid Illicium Verum P.E. Shikimic acid methyl esther 3,4,5-Trihydroxycyclohex-1-enecarboxylic acid 3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid (3R,4S,5R)-3,4,5-TRIHYDROXY-1-CYCLOHEXENECARBOXYLIC ACID (3R,4S,5R)-3,4,5-TRIHYDROXY-CYCLOHEX-1-ENECARBOXYLIC ACID (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid Shikimic acid,(3R,4S,5R)-()-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
CAS	138-59-0
EINECS	205-334-2
InChI	InChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/p-1/t4-,5-,6-/m1/s1
InChIKey	JXOHGGNKMLTUBP-HSUXUTPPSA-N

Shikimic acid - Physico-chemical Properties

Molecular Formula	C7H10O5
Molar Mass	174.15
Density	1.52 g/cm3 (27.2℃)
Melting Point	185-187 °C (lit.)
Boling Point	225.11°C (rough estimate)
Specific Rotation(α)	-180 º (c=4, H2O 25 ºC)
Flash Point	210.1°C
Water Solubility	18 g/100 mL (20 ºC)
Solubility	Easily soluble in water, hardly soluble in chloroform, benzene and petroleum ether.
Vapor Presure	4.45E-08mmHg at 25°C
Appearance	White fine powder
Color	White to light beige or light gray
Merck	14,8480
BRN	4782717
pKa	pK (14.1°) 5.19
Storage Condition	2-8°C
Sensitive	Hygroscopic
Refractive Index	-180 ° (C=1, H2O)
MDL	MFCD00066278
Physical and Chemical Properties	Melting point 185-191°C specific optical rotation -180 ° (c = 4, H2O 25°C) water-soluble 18g/100 mL (20°C)
Use	Is a kind of anti-tumor drugs, but also dioxamycin, glyoxal enzyme inhibitors and other anti-tumor drugs synthetic raw materials

Shikimic acid - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany	3
RTECS	GW4600000
FLUKA BRAND F CODES	3-10
HS Code	29181980
Toxicity	LD5 i.p. in mice: 1000 mg/kg (Evans, Osman)

Shikimic acid - Reference

Reference

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Shikimic acid - Reference Information

Introduction	shikimic acid is a water-soluble white crystalline powder. It was first isolated from Japanese shikima and named, is an important metabolite of plants and microorganisms. For a long time, shikimic acid is mainly extracted from dried and mature fruits of star anise or Japanese shikimia (Japanese anise), in recent years, studies on the extraction of shikimic acid from the fruits of North American liquidambar and pine needles have also been reported.
plant origin	shikimic acid is present in the dried mature fruit of the Magnoliaceae plant. Star anise is a kind of evergreen tree grown in a humid, warm and semi-yin environment, high to 30 meters. Mainly distributed in Fujian, Guangdong, Guangxi, Yunnan, Guizhou and other provinces in the mountain soil. The bark was gray to red-brown in color. The whole margin was single-lobed, grown in the shape of a needle, the leaves were leathery, short-stem, 6-12cm in length and 2-5cm in width, with transparent oil spots on the upper surface. Flowering in spring and autumn. The flowers were single in the axilla of the leaf. There are 3 yellow-green sepals; 6-9 flowers, pink to deep red. Autumn to spring of the second year. The aggregate fruit is star-shaped, octagonal, 1-2cm long, 3-5cm wide, <1cm high. Mature from green to yellow. Mango tips are blunt or blunt-pointed, each containing one seed 6mm long. The fruits are picked in autumn and winter and are red-brown or yellow-brown after drying. The smell is aromatic and sweet. Shikimia, also known as Wild star anise, is a shrub, Evergreen, the seeds are light brown, shiny, flowering 5 months, the fruit period from 9 to 10 months, mainly distributed in the less than 1200 in the desert slope of the forest, autumn results, the fruit contains a large amount of shikimic acid, the fruit is very similar to the anise, but toxic, should avoid confusion.
properties	white powder, soluble in water, solubility in water is 18g/100ml, insoluble in chloroform, benzene and petroleum ether. Melting point 185 ℃ ~ 191 ℃, optical rotation -180 °, odor caprylic acid.
key feedstock for the production of Tamiflu	shikimic acid is a key feedstock for the production of Tamiflu by Roche. Shikimic acid, which is currently used in Roche, is processed and extracted from anise. The steps of synthesizing shikimic acid from petrochemical raw materials are complex, and there is no production and application value except scientific research at present. Shikimic acid can be synthesized from another natural product, quinic acid, which requires several steps of reaction. Quinic acid is derived from the bark of cinchona tree and can be extracted and supplied in large quantities like shikimic acid. The origin of the cinchona tree is mainly in the African country Zaire, but due to the political instability in ZRA, it is difficult to commercially ensure the supply of cinchona bark. At present, another method for producing shikimic acid is to use the method of biological fermentation, and glucose is used as the raw material. This is the second production scheme prepared by Roche in the production of Tamiflu to prevent the instability of the source of star anise (shikimic acid). Roche's fermentation method shikimic acid is produced in northern Europe. The production of shikimic acid by fermentation has been stopped due to the loss of high production costs. Roche claims that 1/3 of its shikimic acid used in Tamiflu production comes from fermentation.
pharmacological effects	shikimic acid inhibits platelet aggregation, arterial and venous thrombosis and cerebral thrombosis by affecting the metabolism of arachidonic acid, it has anti-inflammatory and analgesic effects, and can also be used as an intermediate of antiviral and anticancer drugs. It also has the effect of preventing avian influenza drugs "Tamiflu" and "influenza.
shikimic acid pathway	shikimic acid pathway is an important metabolic pathway in plants, fungi and microorganisms, there are seven enzymatic processes in this pathway. Dehydroquinic acid (DHQ) and shikimate dehydrogenase (SDH) promote stages 3 and 4 in the shikimate pathway. In most microorganisms, DHQ and SDH are monofunctional, but in plants DHQ and SDH can fuse to form enzymes with both functions. The advantage of the DHQ-SDH bifunctional enzyme is that it increases the efficiency of metabolite circulation in the shikimate pathway by limiting the quality of the intermediate in the competitive pathway. Christendat's team at the University of Toronto recently analyzed the structure of DHQ-SDH of Arabidopsis, an herb. The researchers first completed the co-crystallization of DHQ-SDH enzyme and shikimic acid by the gas phase suspension method, and then added nicotinamide adenine dinucleotide phosphate (NADP) to the crystal to form a triple complex. The production of dehydroshikimic acid product at DHQ site indicates that SDH-shikimic acid-NADP(H) is an active complex conducive to the oxidation of shikimic acid, and DHQ-SDH of the concave structure has active site. The DHQ-SDH protein can distinguish metabolites in the shikimate pathway by face-to-face localization and can increase the efficiency of transfer of metabolites from DHQ to the SDH domain. This model has been confirmed by the existing kinetic data, and it is believed that SDH plays a role in the storage of metabolites in the shikimic acid pathway.
Chemical properties	soluble in water, insoluble in chloroform, benzene and petroleum ether. Dry, mature fruit derived from the Magnoliaceae plant Illicium verum.
purpose	is an anti-tumor drug, and is also a kind, glyoxalase inhibitors and other anticancer drug synthesis raw materials shikimic acid is a key precursor for the synthesis of many alkaloids, aromatic amino acids, indole derivatives and chiral drugs. More recently, shikimic acid has been used as A starting material for oseltamivir, the active ingredient of Tamiflu, A neuraminidase inhibitor that is useful for the treatment and prevention of influenza A and influenza B. used as a standard for quantitative determination of shikimic acid content in root apical portion. It was also used as a substrate for the shikimate kinase assay.
production method	shikimic acid is a monomer compound extracted from traditional Chinese medicine star anise.
category	toxic substances
toxicity grade	poisoning
Acute toxicity	intraperitoneal-mouse LD50: 600 mg/kg
flammability hazard characteristics	flammable, spicy and irritating smoke
storage and transportation characteristics	warehouse low temperature, ventilation, dry
extinguishing agent	water, carbon dioxide, dry powder, sand
NIST chemical information	information provided by: webbook.nist.gov (external link)
(IARC) carcinogen classification	3 (Vol. 40, Sup 7) 1987
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)