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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 8742作成日：2026年10月27日

シキミ酸

シキミ酸 · (3R,4S,5R)-(-)-3,4,5-トリヒドロキシ-1-シクロヘキセン-1-カルボン酸 · （3R，4S，5R）-3，4，5-トリヒドロキシシクロヘキサ-1-エン-1-カルボン酸 · (-)-シキミン酸 · シキミ酸, 結晶 · (3R,4S,5R)-3,4,5-トリヒドロキシ-1-シクロヘキセン-1-カルボン酸 · (3R)-3β,4β,5α-トリヒドロキシ-1-シクロヘキセン-1-カルボン酸 · (-)-シキミ酸

https://huagongshe.com/ja/chemical/8742

シキミ酸 の分子構造式

識別子と物理属性

CAS No.138-59-0
分子式C7H10O5
平均分子量174.15 g/mol
単同位体質量174.05282342 g/mol
SMILESO=C(O)C1=C[C@@H](O)[C@@H](O)[C@H](O)C1
InChIKeyJXOHGGNKMLTUBP-HSUXUTPPSA-N
PubChem CID8742
ChEMBLCHEMBL290345
ChEBICHEBI:16119
EC No.205-334-2
DTXSIDDTXSID4032039
現地名シキミ酸

化学・物理的性質

XLogP-1.7
極性表面積98
水素結合供与体数4
水素結合受容体数5
回転可能結合数1
重原子数12
形式電荷0
複雑度222
物質分類Other Classes -> Organic Acids
Color/FormNeedles from methanol/ethyl acetate
溶解度Water solubility = 1.5X10+5 mg/l @ 21 °CSolubility in water about 18 g/100 mlsolubility @ 23 °C (g/100 ml): 2.25 in absolute alcohol, 0.015 in anhydrous etherpractically insoluble in chloroform, benzene, petroleum ether150 mg/mL at 21 °C180g/リットル18g/100mL(20℃)
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
融点183-184.5 °C186 °C185-187 °C (lit.)
蒸気圧0.00000001 [mmHg]0Pa at 25℃
Physical DescriptionSolid[Merck Index] White powder[MSDSonline]
Dissociation ConstantsK = 7.1X10-5 at 14.1 °C
Collision Cross Section149.5 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]136.3 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]137.7 Ų [M-H]-
Other Experimental PropertiesSUBLIMESSPECIFIC 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 ACETATEMP: 191-192 °CMAX ABSORPTION (ETHANOL): 212 NM (E= 8200) /(+ OR -)-FORM/
比旋光度-180 º (c=4, H2O 25 ºC)
沸点225.11°C (rough estimate)
密度1.52 g/cm3 (27.2℃)
屈折率-180 ° (C=1, H2O)
貯蔵条件2-8°C
外観・状態粉
pKa（酸解離定数）pK (14.1°) 5.19
色ホワイトからライトベージュまたはライトグレー
Merck14,8480
BRN4782717
ヘンリー定数3.7×108 mol/(m3Pa) at 25℃, HSDB (2015)
主な用途食品および飲料
化粧品成分の機能スキンコンディショニングデオドラント抗脂漏性
InChI1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
InChIKeyJXOHGGNKMLTUBP-HSUXUTPPSA-N
SMILESO[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
LogP（分配係数）-1.5 at 21℃ and pH1
表面張力49.86mN/m at 1g/L and 20℃
CAS データベース138-59-0(CAS DataBase Reference)
NISTの化学物質情報Shikimic acid(138-59-0)

化学的特性

White Solid

安全性と法規制

GHS 分類This chemical does not meet GHS hazard criteria for 8.3% (3 of 36) of reports.DangerH318 (86.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)Aggregated GHS information provided per 36 reports by companies from 4 notifications to the ECHA C&L Inventory.
規制情報REACH registered substance: (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid (EC: 205-334-2)1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)-: Does not have an individual approval but may be used under an appropriate group standard
有害性の概要May cause irritation[MSDSonline] Intraperitoneal LD50 (mouse) = 1,000 mg/kg[HSDB]
Special ReportsSTAVRIC B, STOLTZ DRSHIKIMIC ACIDFOOD 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.
Hazard Classes and CategoriesEye Dam. 1 (86.1%)
処分方法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.
環境中動態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

用途

解説

(3R,4S,5R)-trihydroxy-1-cyclohexene-1-carboxylic acid．C7H10O5(174.15)．シキミ酸は，シキミIllicium religiosumの果実から見いだされたのでこの名称がある．多くの植物中にキナ酸とともに分布している．無色の針状晶．植物体において、芳香族化合物やリグニンの中間体として機能する有機化合物。融点190～191 ℃．d154 1.599．[α]D－157°(メタノール)．λmax 213 nm(ε 8.9×103)．pKa 4.15．シキミ酸は植物体内でキナ酸とともにヘプトース誘導体の閉環によって生成し，芳香族化合物の生合成の重要な中間体である．近年、インフルエンザ治療薬オセルタミビル（商品名タミフル）の原料として用いられる。LD50 1000 mg/kg(マウス，腹腔)．ラセミ体の融点191～192 ℃．森北出版「化学辞典（第2版）

説明

Shikimic acid (3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid) is a natural organic compound. Plant and microbial sources are the only sources of this compound. The isolation of shikimic acid from the fruit of Illicium religiosum was primarily reported by Ekmann in 1885. The name shikimic acid was derived from the oriental plant shikimi-no-ki in Japanese. It is now available in more quantities through the extraction from the fruit Illicium verum (Chinese star anise). This compound is generally utilized as a starting material for the industrial synthesis of the antiviral oseltamivir, a drug against the H1N1 influenza virus. It is also an essential intermediate in the biosynthesis of lignin, aromatic amino acids (phenylalanine, tyrosine, and tryptophan), and most alkaloids of plants and microorganisms[1]. The neuraminidase inhibitors oseltamivir or Tamiflu derived from the shikimic acid pathway are potent influenza viral neuraminidase inhibitors against most influenza strains ( influenza A and B infections). The mode of application is by mouth, either in the form of a pill or liquid.

使用

Shikimic acid has been used as a standard for the quantification of shikimate in apical parts of roots. It has also been used as a substrate in shikimate kinase assay.

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
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).
Soil Adsorption/MobilityThe 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).
Natural Pollution SourcesShikimic acid as been identified as a component of bracken fern, Pteridium aquilinum(1).
Artificial Pollution SourcesShikimic 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).
Environmental BiodegradationAt 100 ppm shikimic acid, the oxygen uptake by selected aerobic bacteria of the genera Pseudomonas, Flavobacterium, Achromobacter, and Xanthomonas (obtained from garden soil, compost, and sediment from a waste lagoon of a petroleum refinery catalytic cracking plant) inoculated in a mineral salt medium was approximately 150 ul after 120 minutes(1). Benthic microorganisms isolated from two types of bottom sediment of eutrophic Lake Jeziorak in Poland were able to utilize shikimic acid as a source of carbon(2).
Carcinogen ClassificationShikimic acidGroup 3: Not classifiable as to its carcinogenicity to humansVolume 40: (1986) Some Naturally Occurring and Synthetic Food Components, Furocoumarins and Ultraviolet Radiation1987
Environmental BioconcentrationAn 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).
Volatilization from Water/SoilThe 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).
Non-Human Toxicity Excerpts...MICE GIVEN SINGLE ADMIN OF COMMERCIALLY PRODUCED SHIKIMIC ACID OF TESTED PURITY...9 OF THESE 14 ANIMALS...DEVELOPED PRECANCEROUS AND CANCEROUS LESIONS INVOLVING THE GLANDULAR GASTRIC MUCOSA AND ALSO MALIGNANT LEUKEMIAS.SHIKIMIC ACID WAS NOT MUTAGENIC IN AMES TEST.INBRED ACL RATS RECEIVED DIET CONTAINING SHIKIMIC ACID AT 0.1% FOR 142 DAYS. DOSE INGESTED PER RAT WAS MORE THAN TWICE THAT CONTAINED IN BRACKEN (PTERIDIUM SP) IN AN AMT SUFFICIENT TO INDUCE TUMORS AT 100% IN FEEDING EXPT. NO TUMORS WERE INDUCED. CARCINOGENICITY OF BRACKEN, AT LEAST IN RATS, IS ATTRIBUTABLE TO (A) SUBSTANCE(S) OTHER THAN SHIKIMIC ACID.
Evidence for CarcinogenicityNo data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
Environmental Abiotic DegradationThe 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.
Probable Routes of Human ExposureThe 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)
F3-10
水環境危害等級（WGK）3
RTECS 番号GW4600000
毒性LD5 i.p. in mice: 1000 mg/kg (Evans, Osman)
税関コード29181980
危険文句（R）36/37/38
化審法(3)-4476, (3)-4491
危険表示Xi
安全措置（S）22-24/25-36-26
危険等級Eye Dam. 1
貯蔵分類11 - Combustible Solids
有害物質データ138-59-0(Hazardous Substances Data)