Shikimic acid

174.15

174.15

4782717

205-334-2

29MS2WI2NU

DTXSID4032039

Needles from methanol/ethyl acetate

29181980

98

-1.51620

White to light beige or light gray Powder

1.52 g/cm3 (27.2℃)

183-184.5 °C

185-187 °C

210.1ºC

-180 ° (C=1, H2O)

H2O: 18 g/100 mL (20 ºC)

-20°C Freezer

4.45E-08mmHg at 25°C

Peritoneal-mouse LD50: 600 mg/kg

Flammable, spicy and irritating smoke emitted from the fire

-180 º (c=4, H2O 25 ºC)

K = 7.1X10-5 at 14.1 °C

149.5 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|140.55 Ų [M-H]- [CCS Type: DT, Method: stepped-field]|136.3 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|137.7 Ų [M-H]-

SUBLIMES; SPECIFIC OPTICAL ROTATION: -161 °C/D (C= 0.57 IN METHANOL), -183.8 DEG @ 18 °C/D (C= 4.03 IN WATER)|NEEDLES FROM METHANOL/ETHYL ACETATE; MP: 191-192 °C; MAX ABSORPTION (ETHANOL): 212 NM (E= 8200) /(+ OR -)-FORM/

3

36/37/38

22-24/25-36-26

GW4600000

Xi

Warehouse low temperature, ventilated, dry

Stable under normal temperatures and pressures.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

STAVRIC B, STOLTZ DR; SHIKIMIC ACID; FOOD COSMET TOXICOL 14: 141 (1976). A REVIEW DISCUSSING NATURAL OCCURRENCE, FORMATION AS AN INTERMEDIATE IN THE SYNTHESIS OF SEVERAL AROMATIC COMPOUNDS FROM CARBOHYDRATES, PHYSICAL PROPERTIES, CHEMICAL STRUCTURE, THE TOXIC COMPONENT OF BRAKEN FERN, CARCINOGENICITY, BIOLOGICAL DISTRIBUTION & ANALYTICAL METHODS USED FOR ITS IDENTIFICATION.

|Danger|H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P337+P313, and P362|Aggregated GHS information provided by 7 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

moderately toxic

LD50 Mouse ip 1,000 mg/kg

Shikimic acid as been identified as a component of bracken fern, Pteridium aquilinum(1).

Shikimic acid's production and use as an active component in the flotation reagent Quebracho, a depressant for carbonates, fluorite, and non-sulfides(1) may result in its release to the environment(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 6(SRC), determined from an experimental water solubility(2,SRC) and a recommended regression-derived equation(3), indicates that shikimic acid is expected to have very high mobility in soil(SRC). Volatilization of shikimic acid from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 2.7X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Shikimic acid is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 5.0X10-9 mm Hg(SRC), determined from a fragment constant method(5). Aerobic biodegradation of shikimic acid by bacteria of the genera Pseudomonas, Flavobacterium, Achromobacter, and Xanthomonas was relatively rapid; oxygen uptake by the bacteria was approximately 150 ul after 120 minutes(6). Also, it was determined that benthic microorganisms isolated from bottom sediment of a eutrophic lake were able to utilize shikimic acid as a source of carbon(7).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 6(SRC), determined from an experimental water solubility(2,SRC) and a recommended regression-derived equation(3), indicates that shikimic acid is not expected to adsorb to suspended solids and sediment in water(SRC). Shikimic acid is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.7X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 0.74(3,SRC), from an experimental water solubility(2,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Aerobic biodegradation of shikimic acid by bacteria of the genera Pseudomonas, Flavobacterium, Achromobacter, and Xanthomonas was relatively rapid; oxygen uptake by the bacteria was approximately 150 ul after 120 minutes(6). Also, it was determined that benthic microorganisms isolated from bottom sediment of a eutrophic lake were able to utilize shikimic acid as a source of carbon(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), shikimic acid, which has an estimated vapor pressure of 5.0X10-9 mm Hg at 25 °C(2,SRC), is expected to exist almost entirely in the particulate phase in the ambient atmosphere. Vapor-phase shikimic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 6.3 hours(3,SRC). Particulate-phase shikimic acid may be physically removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of shikimic acid with photochemically-produced hydroxyl radicals has been estimated as 6.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 6.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Shikimic acid is not expected to undergo hydrolysis(SRC) or direct photolysis in the environment due to the lack of functional groups to hydrolyze(3) or absorb in the environmental spectrum, respectively.

An estimated BCF value of 0.74 was calculated for shikimic acid(SRC), using an experimental water solubility of 1.5X10+5 mg/l(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

The Koc of shikimic acid is estimated as approximately 6(SRC), using a measured water solubility of 1.5X10+5 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that shikimic acid is expected to have very high mobility in soil(SRC).

The Henry's Law constant for shikimic acid is estimated as 2.7X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that shikimic acid will be essentially nonvolatile from water surfaces(2,SRC). Shikimic acid's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected(SRC). Shikimic acid is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 5.0X10-9 mm Hg(SRC), determined from a fragment constant method(3).

The most probable human exposure to shikimic acid would be occupational exposure, which may occur through dermal contact at workplaces where it is produced or used. The general population will be exposed to shikimic acid via ingestion of food and drinking water and other products containing shikimic acid. (SRC)

SHIKIMIC ACID IS METABOLIZED INTO CYCLOHEXANECARBOXYLIC ACID BY THE INTESTINAL MICROFLORA, BUT THE AROMATIZATION OF CYCLOHEXANECARBOXYLIC ACID OCCURS IN MAMMALIAN TISSUES. IN RATS, THIS ACID IS METABOLIZED AND EXCRETED IN THE URINE MAINLY AS HIPPURIC ACID, TOGETHER WITH 3,4,5,6-TETRAHYDROHIPPURIC ACID & HEXAHYDROHIPPURIC ACID AND SMALL AMT OF BENZOYL & CYCLOHEXYLCARBONYL GLUCURONIDES.|RATS METABOLIZED (14)C-LABELED SHIKIMIC ACID TO HIPPURIC ACID & CATECHOL IN VIVO; RAT CECAL CONTENTS CONVERTED IT TO CYCLOHEXANECARBOXYLIC ACID IN VITRO, THIS CONVERSION BEING ALMOST TOTALLY INHIBITED BY ANTIBIOTICS.

Acid, Shikimic

HPLC WAS USED TO DETECT SHIKIMIC ACID IN WINES & FRUIT JUICES.