Abscisic aldehyde

Base Information

• Chemical Name: Abscisic aldehyde
• CAS No.: 41944-86-9
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• UNII: BDU56T3CXY
• DSSTox Substance ID: DTXSID101045385
• Metabolomics Workbench ID: 28230
• Nikkaji Number: J489.427H
• Wikidata: Q13476484
• Wikipedia: Abscisic_aldehyde
• Mol file: 41944-86-9.mol

Synonyms:Abscisic aldehyde;(+)-abscisic aldehyde;41944-86-9;(+)-cis-abscisic aldehyde;(2Z,4E)-5-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienal;(+)-Abscisyl aldehyde;BDU56T3CXY;Abscisic aldehyde, (+)-;(2Z,4E)-5-((1S)-1-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadienal;2,4-Pentadienal, 5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-, (S-(Z,E))-;(+)-cis-ABA aldehyde;UNII-BDU56T3CXY;SCHEMBL98690;2-cis-(+)-abscisic aldehyde;(+)-cis-abscisic acid aldehyde;CHEBI:31157;DTXSID101045385;LMPR0103050004;Q13476484

Chemical Property of Abscisic aldehyde

Chemical Property:

• Melting Point: >117oC (dec.)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 452

Purity/Quality:

99% ^*data from raw suppliers

(+)-AbscisicAldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=O)CC(C1(C=CC(=CC=O)C)O)(C)C
• Isomeric SMILES: CC1=CC(=O)CC([C@]1(/C=C/C(=C\C=O)/C)O)(C)C
• Uses: Abscisic Aldehyde, is an intermediate in the biosynthesis of the plant hormone Abscisic Acid (A110000). It is also the biosynthetic precursor of phytohormone Abscisic Acid (ABA), which regulates stress responses and controls numerous aspects of plant grow

Technology Process of Abscisic aldehyde

There total 14 articles about Abscisic aldehyde 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: 84.0%

(+)-abscisyl alcohol (56298-25-0) → (2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal (41944-86-9)

Guidance literature:

With manganese(IV) oxide; In ethyl acetate; Petroleum ether; for 1h; Ambient temperature;

DOI:10.1080/00397919708006821

Reference yield: 74.0%

(S)-1-((1E,3Z)-5-Hydroxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclohex-2-ene-1,4-diol → (2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal (41944-86-9)

Guidance literature:

With manganese(IV) oxide; In ethyl acetate; Petroleum ether; for 1h; Ambient temperature;

DOI:10.1080/00397919708006821

Reference yield:

(2Z,4E)-5-<(1S,4S)-1,4-Dihydroxy-2,6,6-trimethyl-2-cyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal (124744-00-9) → (2Z,4E)-5-<(S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal (41944-86-9)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1002/hlca.19890720222

upstream raw materials:

(+)-abscisyl alcohol

(2Z,4E)-5-<(1S,4S)-1,4-Dihydroxy-2,6,6-trimethyl-2-cyclohex-2-en-1-yl>-3-methylpenta-2,4-dienal

methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol

Abscisic acid

Downstream raw materials:

methyl (1'S,2Z,4E,4'S)-5-(1,4-dihydroxy-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-ol

(+)-abscisyl alcohol

Abscisic acid

Refernces

• 1、 Rose,Abrams,Shaw. "Synthesis of chiral acetylenic analogs of the plant hormone abscisic acid". . p. 443 - 450. Retrieved 2007/10/02.
• 2、 Kienzle,Mayer,Minder,Thommen. "Synthesis of optically active natural carotenoids and structurally related compounds. III. Synthesis of (+)-abscisic acid, (-)-xanthoxin, (-)-loliolide, (-)-actinidiolide, and (-)-dihydroactinidiolide". . p. 2616 - 2627. Retrieved 2007/10/10.