Date published: 2026-5-2

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Nicotianamine (CAS 34441-14-0)

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Alternate Names:
(αS,2S)-α-[[(3S)-3-Amino-3-carboxypropyl]amino]-2-carboxy-1-azetidinebutanoic Acid; [2S-[1[αR*(R*)],2R*]]-α-[(3-Amino-3-carboxypropyl)amino]-2-carboxy- 1-azetidinebutanoic Acid
Application:
Nicotianamine is an iron chelating phytosiderophore
CAS Number:
34441-14-0
Purity:
95%
Molecular Weight:
303.31
Molecular Formula:
C12H21N3O6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Nicotianamine functions as a chelator, effectively binding to essential metal ions like iron, copper, and zinc that are for the growth and development of plants. By forming complexes with these metal ions, it aids in their transportation across the cell membrane. Moreover, Nicotianamine exhibits antioxidant properties, shielding cells from oxidative harm and serving as a protective agent.


Nicotianamine (CAS 34441-14-0) References

  1. Nicotianamine preferentially inhibits Angiotensin I-converting enzyme.  |  Hayashi, A. and Kimoto, K. 2007. J Nutr Sci Vitaminol (Tokyo). 53: 331-6. PMID: 17934238
  2. Metal movement within the plant: contribution of nicotianamine and yellow stripe 1-like transporters.  |  Curie, C., et al. 2009. Ann Bot. 103: 1-11. PMID: 18977764
  3. Nicotianamine in zinc and iron homeostasis.  |  Hofmann, NR. 2012. Plant Cell. 24: 373. PMID: 22374391
  4. Determination of nicotianamine in soy sauce and other plant-based foods by LC-MS/MS.  |  Yamaguchi, H. and Uchida, R. 2012. J Agric Food Chem. 60: 10000-6. PMID: 23025624
  5. Nicotianamine is a major player in plant Zn homeostasis.  |  Clemens, S., et al. 2013. Biometals. 26: 623-32. PMID: 23775667
  6. Rice nicotianamine synthase localizes to particular vesicles for proper function.  |  Nozoye, T., et al. 2014. Plant Signal Behav. 9: PMID: 24704865
  7. Nicotianamine is a novel angiotensin-converting enzyme 2 inhibitor in soybean.  |  Takahashi, S., et al. 2015. Biomed Res. 36: 219-24. PMID: 26106051
  8. The Nicotianamine Synthase Gene Is a Useful Candidate for Improving the Nutritional Qualities and Fe-Deficiency Tolerance of Various Crops.  |  Nozoye, T. 2018. Front Plant Sci. 9: 340. PMID: 29636757
  9. Nicotianamine Synthesis by OsNAS3 Is Important for Mitigating Iron Excess Stress in Rice.  |  Aung, MS., et al. 2019. Front Plant Sci. 10: 660. PMID: 31231401
  10. Nicotianamine-chelated iron positively affects iron status, intestinal morphology and microbial populations in vivo (Gallus gallus).  |  Beasley, JT., et al. 2020. Sci Rep. 10: 2297. PMID: 32041969
  11. Nicotianamine Synthase 2 Is Required for Symbiotic Nitrogen Fixation in Medicago truncatula Nodules.  |  Escudero, V., et al. 2019. Front Plant Sci. 10: 1780. PMID: 32082345
  12. The ancient roots of nicotianamine: diversity, role, regulation and evolution of nicotianamine-like metallophores.  |  Laffont, C. and Arnoux, P. 2020. Metallomics. 12: 1480-1493. PMID: 33084706
  13. Iron uptake mediated by the plant-derived chelator nicotianamine in the small intestine.  |  Murata, Y., et al. 2021. J Biol Chem. 296: 100195. PMID: 33334885
  14. Overexpression of Nicotianamine Synthase (AtNAS1) Increases Iron Accumulation in the Tuber of Potato.  |  Zha, M., et al. 2022. Plants (Basel). 11: PMID: 36297765

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Nicotianamine, 1 mg

sc-219356
1 mg
$547.00

Nicotianamine, 2 mg

sc-219356A
2 mg
$1022.00

Nicotianamine, 5 mg

sc-219356B
5 mg
$2289.00

Nicotianamine, 10 mg

sc-219356C
10 mg
$4162.00

What is the method of production? Chemical or enzymatic?

Asked by: james21
Thank you for your question. The production is based on chemical synthesis. Unfortunately, we are not able to provide you with the synthetic route, since it is confidential information.
Answered by: Technical Support
Date published: 2019-09-11

should I detect the molecule in HPLC, at what wavelength should I observe it?

Asked by: Vale
Thank you for your question. This product is not UV active and will have a low response if UV is used for detection. For low UV detection materials, we recommend using ESLD instead of UV.
Answered by: Technical Support
Date published: 2019-04-26

Hi, I would like to purchase nicotianamine, sc-219356. Could you let me know the price for shipping and how long it would take to get here? Thanks Penny

Asked by: Penelope
Thank you for your question. Please contact our Customer Care Department to inquire about current product availability and shipping lead times to Australia. Please call us toll-free at (800) 457-3801 option 1, e-mail <customercare@scbt.com>, or use the live chat on our website. Alternatively, please contact one of our authorized distributors in Australia. You can search for their contact information using the link below. https://www.scbt.com/scbt/resources/distributors
Answered by: Technical Support
Date published: 2017-11-15

What is the solubility in water?

Asked by: chemsd02
Thank you for your question. sc-219356 (Nicotianamine, CAS 34441-14-0) has a solubility of 1-2 mg/mL in water.
Answered by: Chemical Support 10
Date published: 2017-03-09
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Rated 5 out of 5 by from Aarts (PubMed ID 25288637) reports that nicotianamineAarts (PubMed ID 25288637) reports that nicotianamine secreted from the roots of Arabidopsis halleri brings about zinc hypertolerance by controlling zinc bioavailability. -SCBT Publication Review
Date published: 2015-05-30
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Nicotianamine is rated 5.0 out of 5 by 1.
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