3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid

Base Information

• Chemical Name: 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
• CAS No.: 2306-23-2
• Molecular Formula: C7H10O5
• Molecular Weight: 174.153
• NSC Number: 59257
• DSSTox Substance ID: DTXSID80859270
• Nikkaji Number: J23.532F
• Wikidata: Q104402824
• Mol file: 2306-23-2.mol

Synonyms:3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid;3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid;2306-23-2;Skikimic acid;3,4,5-Trihydroxycyclohex-1-enecarboxylic acid;3,4,5-trihydroxycyclohexene-1-carboxylic acid;ShikimicAcid;Bracken fern toxic component;1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-;1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, [3R-(3.alpha.,4.alpha.,5.beta.)]-;MFCD00066278;NSC-59257;SCHEMBL43376;MLS006011822;DTXSID80859270;CHEBI:132329;HMS3656I09;WLN: L6UTJ AVQ CQ DQ EQ;NSC59257;BBL015141;STK803139;AKOS003382835;AS-12993;SMR004703495;SY057997;EN300-138752;F14844;3,5-Trihydroxy-1-cyclohexene-1-carboxylic acid;1-Cyclohexene-1-carboxylic acid,4,5-trihydroxy-;1-Cyclohexene-1-carboxylic acid,4,5-trihydroxy-, [3R-(3.alpha.,4.alpha.,5.beta.)]-;1-Cyclohexene-1-carboxylic acid,4,5-trihydroxy-, labeled with carbon-14, (-)-

Chemical Property of 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid

Chemical Property:

• PSA: 97.99000
• LogP: -1.51620
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 174.05282342
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C=C1C(=O)O)O)O)O

Technology Process of 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid

There total 17 articles about 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

ethyl (3S,4S,5S)-3,4,5-trihydroxy-cyclohex-1-ene-1-carboxylate → (3S,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid (138-59-0,2306-23-2,10191-00-1,15271-51-9,16661-31-7,21967-35-1,90761-07-2)

Guidance literature:

With sodium hydroxide; In methanol; at 40 ℃; for 10h;

DOI:10.1002/ejoc.202100653

Reference yield:

(-)-(1S)-1-{(4S,5S)-5-[(1S)-1-hydroxy-2-propenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propen-1-ol (261631-95-2) → (3S,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid (138-59-0,2306-23-2,10191-00-1,15271-51-9,16661-31-7,21967-35-1,90761-07-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / Inert atmosphere; Reflux

1.2: 1 h / 0 - 20 °C / Inert atmosphere

2.1: 16 h / 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / water / 12 h / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; trifluoroacetic acid; In dichloromethane; water;

DOI:10.1021/jo402764v

Reference yield:

(1R,2R,3S,4S)-1-chloro-2-acetoxy-3,4-(isopropylidenedioxy)-cyclohex-5-ene (1582805-94-4) → (3S,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid (138-59-0,2306-23-2,10191-00-1,15271-51-9,16661-31-7,21967-35-1,90761-07-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 16 h / 20 °C / Inert atmosphere

2: trifluoroacetic acid / water / 12 h / Inert atmosphere

With trifluoroacetic acid; In water;

DOI:10.1021/jo402764v

upstream raw materials:

(1R,2R,3S,4S)-1-chloro-2-acetoxy-3,4-(isopropylidenedioxy)-cyclohex-5-ene

(3aR,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole

(3aR,4S,5aR,6aR,6bS)-2,2-dimethylhexahydrooxireno[2′,3′:3,4]-benzo[1,2-d][1,3]dioxol-4-ol

(3aS,5aS,6aS,6bS)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole