Record Information
Version1.0
Creation date2010-04-08 22:05:17 UTC
Update date2020-09-17 15:39:36 UTC
Primary IDFDB002239
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(E)-Zeatin
DescriptionCis-zeatin, also known as (e)-zeatin or trans-zeatin, belongs to the class of organic compounds known as 6-alkylaminopurines. 6-alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. An aminopurine factor in plant extracts that induces cell division. Cis-zeatin is a strong basic compound (based on its pKa). Outside of the human body, Cis-zeatin is found, on average, in the highest concentration within corns. Cis-zeatin has also been detected, but not quantified in, several different foods, such as green zucchinis, adzuki beans, scarlet beans, white lupines, and jicama. This could make cis-zeatin a potential biomarker for the consumption of these foods. Zeatin is a plant hormone derived from the purine adenine. Zeatin was first discovered in immature corn kernels from the genus Zea. As in the case of kinetin, zeatin has also been reported to have several in vitro anti-aging effects on human skin fibroblasts. Zeatin and derivatives were discovered to be the primary active ingredient in coconut milk, which has long been known to actively induce plant growth. It is a member of the plant growth hormone family known as cytokinins.
CAS Number1637-39-4
Structure
Thumb
Synonyms
SynonymSource
(2E)-2-Methyl-4-(1H-purin-6-ylamino)-2-buten-1-olbiospider
(2E)-2-Methyl-4-(9H-purin-6-ylamino)but-2-en-1-olbiospider
(E)-2-Methyl-4-(1H-purin-6-ylamino)-2-buten-1-olbiospider
(E)-2-Methyl-4-(1H-purin-6-ylamino)but-2-en-1-olbiospider
(E)-2-Methyl-4-(purin-6-ylamino)-2-buten-1-olbiospider
(E)-Zeatinbiospider
2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (2E)-biospider
2-Buten-1-ol, 2-methyl-4-(1H-purin-6-ylamino)-, (E)-biospider
2-buten-1-ol, 2-methyl-4-(9H-purin-6-ylamino)-, (2E)-biospider
2-Buten-1-ol, 2-methyl-4-(purin-6-ylamino)-, (E)-biospider
trans-Zeatinbiospider
Zeatinmanual
Predicted PropertiesNot Available
Chemical FormulaC10H13N5O
IUPAC name
InChI IdentifierInChI=1S/C10H13N5O/c1-7(4-16)2-3-11-9-8-10(13-5-12-8)15-6-14-9/h2,5-6,16H,3-4H2,1H3,(H2,11,12,13,14,15)/b7-2+
InChI KeyUZKQTCBAMSWPJD-FARCUNLSSA-N
Isomeric SMILESC\C(CO)=C/CNC1=NC=NC2=C1NC=N2
Average Molecular Weight219.2431
Monoisotopic Molecular Weight219.112010063
Classification
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.78%; H 5.98%; N 31.94%; O 7.30%DFC
Melting PointMp 212-213° (207-208°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data276 (e 14650) (NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00371
Pubchem Compound ID449093
Pubchem Substance IDNot Available
ChEBI ID16522
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCHJ21-Q:CHJ22-R
EAFUS IDNot Available
Dr. Duke IDTRANS-ZEATIN|ZEATIN
BIGG IDNot Available
KNApSAcK IDC00000091
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDZeatin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
mitoticDUKE
phytohormonal26158 A plant growth regulator that modulates the formation of stems, leaves and flowers, as well as the development and ripening of fruit. The term includes endogenous and non-endogenous compounds (e.g. active compounds produced by bacteria on the leaf surface) as well as semi-synthetic and fully synthetic compounds.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).