| Identification | More | [Name]
Shikimic acid | [CAS]
138-59-0 | [Synonyms]
1-CYCLOHEXENE-1-CARBOXYLIC ACID, 3,4,5-TRIHYDROXY-, (3R,4S,5R)
3,4,5-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACID
(-)3ALPHA,4ALPHA,5BETA-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC 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-TRIHYDROXYL-1-CYCLOHEXENE-1-CARBOXYLIC ACID
(3R,4S,5R)-TRIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACID
L-SHIKIMIC ACID
(-)-SHIKIMIC ACID
SHIKIMIC ACID
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, [3R-(3alpha,4alpha,5beta)]-
Bracken fern toxic component
Shikimate
Skikimic acid
Kava Kava Extract
3,4,5-Trihydroxy-1-Cyclohexene-1-Carboxylic Acid (Shikimic acid)
Shikimic
(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
SHIKIMIC ACID 98% | [EINECS(EC#)]
205-334-2 | [Molecular Formula]
C7H10O5 | [MDL Number]
MFCD00066278 | [Molecular Weight]
174.15 | [MOL File]
138-59-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
185-187 °C (lit.) | [alpha ]
-180 º (c=4, H2O 25 ºC) | [Boiling point ]
225.11°C (rough estimate) | [density ]
1.52 g/cm3 (27.2℃) | [vapor pressure ]
0Pa at 25℃ | [refractive index ]
-180 ° (C=1, H2O) | [storage temp. ]
2-8°C | [solubility ]
180g/l | [form ]
Powder | [pka]
pK (14.1°) 5.19 | [color ]
White to light beige or light gray | [Optical Rotation]
[α]/D -180.0±5.0°, c = 4 in H2O | [Water Solubility ]
18 g/100 mL (20 ºC) | [Sensitive ]
Hygroscopic | [Usage]
Naturally occurring (-)-form is a major biosynthetic precursor of phenylalanine, tyrosine, and tryptophan and hence of the majority of plant alkaloids. It is also involved in the biosynthesis of lignin, flavonpids and other important aromatic compou | [Detection Methods]
HPLC | [Merck ]
14,8480 | [BRN ]
4782717 | [Henry's Law Constant]
3.7×108 mol/(m3Pa) at 25℃, HSDB (2015) | [Major Application]
food and beverages | [Cosmetics Ingredients Functions]
SKIN CONDITIONING
DEODORANT
ANTI-SEBORRHEIC | [InChI]
1S/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 | [InChIKey]
JXOHGGNKMLTUBP-HSUXUTPPSA-N | [SMILES]
O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O | [LogP]
-1.5 at 21℃ and pH1 | [Surface tension]
49.86mN/m at 1g/L and 20℃ | [CAS DataBase Reference]
138-59-0(CAS DataBase Reference) | [IARC]
3 (Vol. 40, Sup 7) 1987 | [NIST Chemistry Reference]
Shikimic acid(138-59-0) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H318 | [Precautionary statements ]
P280-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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
| [F ]
3-10 | [REACH Registrations]
Active | [HS Code ]
29181980 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Dam. 1 | [Hazardous Substances Data]
138-59-0(Hazardous Substances Data) | [Toxicity]
LD5 i.p. in mice: 1000 mg/kg (Evans, Osman) |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
White Solid | [Uses]
Naturally occurring (-)-form is a major biosynthetic precursor of phenylalanine, tyrosine, and tryptophan and hence of the majority of plant alkaloids. It is also involved in the biosynthesis of lignin, flavonpids and other important aromatic compounds. | [Definition]
ChEBI: A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). It is an intermediate metabolite in plants and micro
rganisms. | [Biochem/physiol Actions]
Shikimic acid is observed to be carcinogenic in rat models, when administered. It serves as a precursor for the biosynthesis of aromatic amino acids, alkaloids and other aromatic metabolites in microorganisms. Shikimic acid is known to inhibit adenosine diphosphate (ADP) induced platelet aggregation and blood coagulation in rabbits. | [storage]
Store at -20°C | [References]
[1] Priyanka Singh. “Shikimic acid as intermediary model for the production of drugs effective against influenza virus.” Phytochemicals as Lead Compounds for New Drug Discovery 14 1 (2020): 245–256. |
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