(2E)-2-methyl-4-[(9H-purin-6-yl)amino]but-2-en-1-ol

• ChemBase ID: 103578
• Molecular Formular: C10H13N5O
• Molecular Mass: 219.24312
• Monoisotopic Mass: 219.11201006
• SMILES: C/C(=C\CNc1ncnc2c1[nH]cn2)/CO
• Canonical SMILES: OC/C(=C/CNc1ncnc2c1[nH]cn2)/C
• InChI: InChI=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)
• InChIKey: UZKQTCBAMSWPJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-2-methyl-4-[(9H-purin-6-yl)amino]but-2-en-1-ol; (2E)-2-methyl-4-[(7H-purin-6-yl)amino]but-2-en-1-ol; 2-methyl-4-[(9H-purin-6-yl)amino]but-2-en-1-ol; 2-methyl-4-[(7H-purin-6-yl)amino]but-2-en-1-ol
• IUPAC Traditional name: trans-zeatin; zeatin
• Synonyms: 6-(4-Hydroxy-3-methylbut-2-enylamino)purine; trans-Zeatin hydrochloride; Zeatin; N6-(4-Hydroxy-3-methyl-2-buten-1-yl)adenine; trans-Zeatin; (2E)-2-Methyl-4-(9H-purin-6-ylamino)-2-buten-1-ol; 6-(4-Hydroxy-3-methyl-trans-2-butenylamino)purine; N6-(4-Hydroxy-3-methyl-trans-2-butenyl)adenine; ZT; ZTA; Zeatin; (E)-Zeatin; Zeatine; trans-Zeatin; 6-[(E)-4-Hydroxy-3-methyl-2-butenylamino] purine; N^6-(4-Hydroxy-3-methyl-2-buten-1-yl)adenine; 6-[4-Hydroxy-3-methylbut-2-enylamino]purine; ZEATIN; 6-(4-羟基-3-甲基丁-2-烯基氨基)嘌呤; N6-(4-羟基-3-甲基-2-丁烯-1-基)腺嘌呤; 反-玉米素 盐酸盐; 反-玉米素

Database IDs

• CAS Number: 6025-81-6; 32771-64-5; 1637-39-4; 13114-27-7
• MDL Number: MFCD00213654
• Beilstein Number: 616241
• PubChem SID: 24902158; 24902177; 24902170; 24890259; 162090867
• PubChem CID: 449093

CALCULATED PROPERTIES

• Acid pKa: 9.867978
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.2835231
• LogD (pH = 7.4): -0.15424982
• Log P: -0.14883372
• Molar Refractivity: 62.9856 cm^3
• Polarizability: 22.93417 Å^3
• Polar Surface Area: 86.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: off-white to yellow powder
• Melting Point: 208-215°C

Safety Information

• Storage Condition: 0°C; 2-8°C
• RTECS: EM9506000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >99.8%; ≥97%; ≥98.0% (HPLC); 97%
• Suitability: plant cell culture tested
• Quality: crystallized
• Empirical Formula (Hill Notation): C10H13N5O

DETAILS

MP Biomedicals - 02153854

(6-[(E)-4-Hydroxy-3-methyl-2-butenylamino] purine) Synthetic trans-isomer White, crystalline needles Purity: >99.8% by HPLC Highly potent growth hormone in plants. Stimulates cell division.

MP Biomedicals - 02152271

cis-isomer
Off-white to yellow powder
May contain up to 10% trans-isomer.

Sigma Aldrich - Z0164

Other Notes
Mixed isomersApprox. 80% trans; balance primarily cis.
Application
Zeatin is a coconut milk-derived plant hormone (cytokinin) that promotes growth of lateral buds, stimulates cell division(Lateral Dominance), callus initiation and seed germination. Zeatin is used with Murashige and Skoog and other media, zeatin promotes multiple shoot generation from internodes and high frequency thick spread roots.

Sigma Aldrich - Z0876

Biochem/physiol Actions
trans-Zeatin-riboside is a plant cytokinin

Sigma Aldrich - Z2753

包装
5 mg in glass bottle

Sigma Aldrich - 96088

Biochem/physiol Actions
trans-Zeatin-riboside is a plant cytokinin

Toronto Research Chemicals - Z273000

Zeatin, purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form. Trans-Zeatin inhibits UVB-induced matrix metalloproteinase-1 expression via MAP kinase signaling

REFERENCES

• Murashige, T., et al.: Physiol. Plant, 15, 473 (1962)
• Brenneisen, P., et al.: J. Biol. Chem., 273, 5279 (1962)
• Choi, M., et al.: J. Dermatol. Sci., 46, 127 (1962)
• Bae, J., et al.: Food Chem. Toxicol., 46, 1298 (1962)