6-Furfurylaminopurine

Base Information

• Chemical Name: 6-Furfurylaminopurine
• CAS No.: 525-79-1
• Deprecated CAS: 33446-70-7,525-80-4,525-80-4
• Molecular Formula: C10H9N5O
• Molecular Weight: 215.214
• Hs Code.: 2933.59
• European Community (EC) Number: 208-382-2
• NSC Number: 23119
• UNII: P39Y9652YJ
• DSSTox Substance ID: DTXSID9035175
• Nikkaji Number: J6.656G
• Wikipedia: Kinetin
• Wikidata: Q2251215
• Metabolomics Workbench ID: 41943
• ChEMBL ID: CHEMBL228792
• Mol file: 525-79-1.mol

Synonyms:1H-Purin-6-amine,N-(2-furanylmethyl)- (9CI);Adenine, N-furfuryl- (7CI,8CI);Adenine,N6-furfuryl- (6CI);2-Furanmethanamine, N-1H-purin-6-yl-;6-(Furfurylamino)purine;6-Furfuryladenine;FAP;KT;Kinetin (planthormone);N-Furfuryladenine;N6-(Furfurylamino)purine;N6-Furfuryladenine;NSC23119;6-Furfurylaminopurine;

Chemical Property of 6-Furfurylaminopurine

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 4.32E-11mmHg at 25°C
• Melting Point: 269-271 °C (dec.)(lit.)
• Refractive Index: 1.7610 (estimate)
• Boiling Point: 524.4 °C at 760 mmHg
• PKA: pKa1 2.7; pKa2 9.9(at 25℃)
• Flash Point: 270.9 °C
• PSA: 79.63000
• Density: 1.489 g/cm³
• LogP: 1.63100
• Storage Temp.: ?20°C
• Solubility.: H2O: soluble
• Water Solubility.: Soluble in water (<1 mg/ml) at 25°C, Acetic acid (49.00-51.00 mg/ml), DMSO (43 mg/ml) at 25°C, ethanol (<1 mg/ml) at 25°C, 0.1 N Sodium hydroxide (1% w/v), methanol (slightly), and dilute aqueous hydrochloric acid or sodium hydroxide (freely).
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 215.08070993
• Heavy Atom Count: 16
• Complexity: 239

Purity/Quality:

99%, ^*data from raw suppliers

Kinetin 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 68-36/37/38
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Plant Growth Regulators
• Canonical SMILES: C1=COC(=C1)CNC2=NC=NC3=C2NC=N3
• Recent ClinicalTrials: The Safety and Tolerability of Kinetin, in Patients With Familial Dysautonomia
• Description: Kinetin (or Vivakin) was introduced as Kinerase in the US as a new ingredient for the treatment of age related photodamage of skin. This 6- furfurylaminopurine is a synthetic cytokinin, a family of plant growth factors, and was shown to be a highly potent growth factor. In vitro, it was able to delay or prevent the onset of age-related changes in skin cells without affecting cellular lifespan. In a double-blind clinical trial, Kinetin (0.005%) partially reversed the clinical signs of photodamaged skin and demonstrated a good safety profile. It could have potential in psoriasis as well as in other proliferative skin disorders. Kinetin is a cytokinin plant growth regulator with diverse biological activities. Kinetin (0.23 μM) increases p34cdc2-like histone H1 kinase activity, the number of cells in mitosis, and total cell number in arrested N. plumbaginifolia cells. It increases GSH levels and activity of glutathione peroxidase and glutathione reductase, but reduces thiobarbituric acid reactive substances (TBARS) levels, in human skin fibroblasts when used at a concentration of 10 μM. Kinetin (40 μM) reduces age-related enlargement, multinucleation, and accumulation of cellular debris in human mammary skin fibroblasts without affecting proliferative lifespan.
• Uses: auxin, plant growth regulator, plant cell division promotor Plant growth accelerator Plant growth regulator. To augment growth of microbial cultures: BE 632589 (1963 to Hoechst). Kinetin acts as plant growth accelerator, auxin, plant growth regulator, plant cell division promotor. It also acts as cell division factor found in various plant parts and in yeast. A plant growth regulator. Augments growth of microbial cultures.

Technology Process of 6-Furfurylaminopurine

There total 34 articles about 6-Furfurylaminopurine 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: 98.0%

furan-2-ylmethanamine (617-89-0) + 6-chloro-7H-purine (87-42-3,111055-92-6) → kinetin (525-79-1,525-80-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1,1,3,3,3-hexamethyl-disilazane; at 110 ℃; for 2h;

Reference yield: 96.7%

furan-2-ylmethanamine (617-89-0) + 6-chloropurine (87-42-3) → kinetin (525-79-1)

Guidance literature:

With triethylamine; In ethanol; for 5h; Reflux;

Reference yield: 90.0%

furan-2-ylmethanamine (617-89-0) + 1,7-dihydro-6H-purin-6-one (68-94-0) → kinetin (525-79-1,525-80-4)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 72h;

DOI:10.1021/jo7020373

upstream raw materials:

furan-2-ylmethanamine

6-chloro-7H-purine

6-(methylthio)-1H-purine

N⁴-furfuryl-pyrimidine-4,5,6-triyltriamine

Downstream raw materials:

furane-2-ylmethyl-(9-trityl-9H-purine-6-yl)-amine

kinetin riboside

furan-2-ylmethanamine

hypoxanthine

Refernces

• 1、 Miller et al.. "-". . p. 1375,1378,1379. Retrieved 1956.
• 2、 -. "INHIBITORS OF LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE (LMPTP) AND USES THEREOF". Paragraph 0205; 0206. . Retrieved 2019/07/20.
• 3、 Wang, Xuebao,Han, Chao,Wu, Kaiqi,Luo, Lu,Wang, Yu,Du, Xuze,He, Qin,Ye, Faqing. "Design, synthesis and ability of non-gold complexed substituted purine derivatives to inhibit LPS-induced inflammatory response". . p. 10 - 21. Retrieved 2018/03/01.