shikimic acid

1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- (9CI)

CAS: 138-59-0 C7 H10 O5 MW: 174.15270000

Identification

Nameshikimic acid
IUPAC(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
CAS Number138-59-0
EINECS205-334-2
FDA UNII29MS2WI2NU
Molecular FormulaC7 H10 O5
Molecular Weight174.15270000
MDL NumberMFCD00066278
Nikkaji NumberJ3.267K
Beilstein2210055

Regulatory

Physical Properties

Appearance white needles or powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 183.00 to 184.50 °C. @ 760.00 mm Hg
Boiling Point 400.00 to 401.00 °C. @ 760.00 mm Hg (est)
Flash Point 410.00 °F. TCC ( 210.10 °C. ) (est)
logP (o/w) -2.220 (est)
Soluble in water, 1.50E+05 mg/L @ 21C (exp)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesantidandruff agents

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 1000 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic agents
Recommendation for shikimic acid usage levels up tonot for fragrance use.
Recommendation for shikimic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

apple plant banana leaf bean mung bean seed black gram sprout buckwheat hypocotyl carrot root celery root cherry sour cherry fruit coconut seed elder black elder plant fennel seed fig fruit ginger leaf ginkgo biloba leaf gooseberry fruit grape leaf grape root mamey leaf parsley root pear fruit pistachio leaf rice leaf sunflower seed

Synonyms

bracken fern toxic component 1- cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- 1- cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- (9CI) (-)- shikimic acid L- shikimic acid skikimic acid (-)-3,4,5- trihydroxy-1-cyclohexene-1-carboxylic acid (3R,4S,5R)-3,4,5- trihydroxy-1-cyclohexene-1-carboxylic acid [3R-(3a,4a,5b)]-3,4,5- trihydroxy-1-cyclohexene-1-carboxylic acid 3,4,5- trihydroxy-1-cyclohexene-1-carboxylic acid (3R,4S,5R)-(-)-3,4,5- trihydroxy-1-cyclohexenecarboxylic acid 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 3,4,5- trihydroxycyclohex-1-ene-1-carboxylic acid (3R,4S,5R)-3,4,5- trihydroxycyclohex-1-enecarboxylic acid (4S,3R,5R)-3,4,5- trihydroxycyclohex-1-enecarboxylic acid (3R,4S,5R)-3,4,5- trihydroxycyclohexene-1-carboxylic acid PubMed: Glyphosate spray drift in Coffea arabica - Sensitivity of coffee plants and possible use of shikimic acid as a biomarker for glyphosate exposure. PubMed: Characterization of phenolic compounds in Brazilian pepper (Schinus terebinthifolius Raddi) Exocarp. PubMed: Protective effect of coconut water concentrate and its active component shikimic acid against hydroperoxide mediated oxidative stress through suppression of NF-κB and activation of Nrf2 pathway. PubMed: Metabolomic analysis of the polyphenols in germinating mung beans (Vigna radiata) seeds and sprouts. PubMed: Metabolic differentiation of diamondback moth ( Plutella xylostella (L.)) resistance in cabbage ( Brassica oleracea L. ssp. capitata). PubMed: Foliar nickel application alleviates detrimental effects of glyphosate drift on yield and seed quality of wheat. PubMed: Metabolome profiling of floral scent production in Petunia axillaris. PubMed: Induced plant defense via volatile production is dependent on rhizobial symbiosis. PubMed: Plants as biofactories: glyphosate-induced production of shikimic acid and phenolic antioxidants in wounded carrot tissue. PubMed: Characterisation of volatile and non-volatile metabolites in etiolated leaves of tea (Camellia sinensis) plants in the dark. PubMed: Composition of sugars, organic acids, and total phenolics in 25 wild or cultivated berry species. PubMed: Three types of ultraviolet irradiation differentially promote expression of shikimate pathway genes and production of anthocyanins in grape berries. PubMed: Shikimate pathway modulates the elicitor-stimulated accumulation of fragrant 2-hydroxy-4-methoxybenzaldehyde in Hemidesmus indicus roots. PubMed: Chemical constituents comparison between Rhizoma Smilacis Glabrae and Rhizoma Smilacis Chinae by HPLC-DAD-MS/MS. PubMed: Development of HPLC fingerprint for species differentiation and quality assessment of Rhizoma Smilacis Glabrae. PubMed: Metabolic discrimination of mango juice from various cultivars by band-selective NMR spectroscopy. PubMed: Pool of resistance mechanisms to glyphosate in Digitaria insularis. PubMed: Antibacterial activity of water-soluble extract from pine needles of Cedrus deodara. PubMed: Characterization and quantification of hydroxycinnamate derivatives in Stevia rebaudiana leaves by LC-MSn. PubMed: Illicium verum: a review on its botany, traditional use, chemistry and pharmacology. PubMed: Effect of aromatic precursor addition to wine fermentations carried out with different Saccharomyces species and their hybrids. PubMed: Evaluation of spectrophotometric and HPLC methods for shikimic acid determination in plants: models in glyphosate-resistant and -susceptible crops. PubMed: Gene expression in the scleractinian Acropora microphthalma exposed to high solar irradiance reveals elements of photoprotection and coral bleaching. PubMed: Development of capillary electrophoresis fingerprint for quality control of rhizoma Smilacis Glabrae. PubMed: An extremely stable and sensitive end-column electrochemical detector based on heated copper microdisk electrode with direct current for CE and CE-Chip. PubMed: Profiling and characterization by LC-MSn of the chlorogenic acids and hydroxycinnamoylshikimate esters in maté (Ilex paraguariensis). PubMed: Sweet cherry pomological and biochemical characteristics influenced by rootstock. PubMed: Bound volatile precursors in genotypes in the pedigree of 'Marion' blackberry (Rubus sp.). PubMed: Glyphosate effect on shikimate, nitrate reductase activity, yield, and seed composition in corn. PubMed: Horseweed with reduced susceptibility to glyphosate found in the czech republic. PubMed: Highly enhanced electrocatalytic oxidation of glucose and shikimic acid at a disposable electrically heated oxide covered copper electrode. PubMed: Nontarget mechanims involved in glyphosate tolerance found in Canavalia ensiformis plants. PubMed: Characterization and quantification of grape variety by means of shikimic acid concentration and protein fingerprint in still white wines. PubMed: Aminomethylphosphonic acid accumulation in plant species treated with glyphosate. PubMed: Enzymes of the shikimic acid pathway encoded in the genome of a basal metazoan, Nematostella vectensis, have microbial origins. PubMed: Shikimic acid accumulation in field-grown corn (Zea mays) following simulated glyphosate drift. PubMed: Novel lipid-peroxidation- and cyclooxygenase-inhibitory tannins from Picrorhiza kurroa seeds. PubMed: Isotopic criteria in the characterization of aromatic molecules. 1. Hydrogen affiliation in natural benzenoid/phenylpropanoid molecules. PubMed: Comparison of cardioprotective abilities between the flesh and skin of grapes. PubMed: New insights on glyphosate mode of action in nodular metabolism: Role of shikimate accumulation. PubMed: Chemical composition and in vitro antimicrobial activities of the essential oils from endemic Psiadia species growing in mauritius. PubMed: Phenolic metabolites from honeybush tea (Cyclopia subternata). PubMed: Aminomethylphosphonic acid, a metabolite of glyphosate, causes injury in glyphosate-treated, glyphosate-resistant soybean. PubMed: Aroma composition of Vitis vinifera Cv. tannat: the typical red wine from Uruguay. PubMed: Glyphosate applied preharvest induces shikimic acid accumulation in hard red spring wheat (Triticum aestivum). PubMed: Antioxidant activity of 3-dehydroshikimic acid in liposomes, emulsions, and bulk oil. PubMed: Shikimate accumulates in both glyphosate-sensitive and glyphosate-resistant horseweed (Conyza canadensis L. Cronq.). PubMed: Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds of glyphosate-treated, glyphosate-resistant soybean. PubMed: Hydrophilic carboxylic acids and iridoid glycosides in the juice of American and European cranberries (Vaccinium macrocarpon and V. oxycoccos), lingonberries (V. vitis-idaea), and blueberries (V. myrtillus). PubMed: LC/MS/MS characterization of phenolic constituents in dried plums. PubMed: Acylated and non-acylated flavonol monoglycosides from the Indian minor spice Nagkesar (Mammea longifolia). PubMed: Study of the organic acids composition of quince (Cydonia oblonga Miller) fruit and jam. PubMed: Tolerance and accumulation of shikimic acid in response to glyphosate applications in glyphosate-resistant and nonglyphosate-resistant cotton (Gossypium hirsutum L.). PubMed: Glyphosate effects on phenolic metabolism of nodulated soybean (Glycine max L. merr.). PubMed: Alkylperoxyl radical-scavenging activity of various flavonoids and other phenolic compounds: implications for the anti-tumor-promoter effect of vegetables. PubMed: Genotoxicity studies of quercetin and shikimate in vivo in the bone marrow of mice and gastric mucosal cells of rats. PubMed: Genetic aspects of aromatic amino acid biosynthesis in Lactococcus lactis. PubMed: Oncogenic and tumor-promoting Spermatophytes and Pteridophytes and their active principles. PubMed: Shikimic acid. PubMed: Determination of organic acids in foods by liquid chromatography. PubMed: (-)-3t,4t-Dihydroxycyclohexane-1c-carboxylate, a new quinate metabolite of Lactobacillus plantarum.