mugineic acid
 
Notes:
None found
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CAS Number: 69199-37-7Picture of molecule3D/inchi
FDA UNII: KR256JY76I
XlogP3-AA: -6.70 (est)
Molecular Weight: 320.29900000
Formula: C12 H20 N2 O8
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for mugineic acid usage levels up to:
 not for fragrance use.
 
Recommendation for mugineic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11067153
National Institute of Allergy and Infectious Diseases: Data
 (2S)-1-[(2S,3S)-3-carboxy-3-[[(3S)-3-carboxy-3-hydroxypropyl]amino]-2-hydroxypropyl]azetidine-2-carboxylic acid
Chemidplus: 0069199377
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References:
 (2S)-1-[(2S,3S)-3-carboxy-3-[[(3S)-3-carboxy-3-hydroxypropyl]amino]-2-hydroxypropyl]azetidine-2-carboxylic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 11067153
Pubchem (cas): 69199-37-7
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
KEGG (GenomeNet): C15500
HMDB (The Human Metabolome Database): HMDB33555
FooDB: FDB012668
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 Hordeum vulgare root
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Synonyms:
1-azetidinebutanoic acid, 2-carboxyl-alpha-((3-carboxy-3-hydroxypropyl)amino)-beta-hydroxy-, (2S-(1(alphaR*(R*),betaR*),2R*))-
(2S)-1-[(2S,3S)-3-carboxy-3-[[(3S)-3-carboxy-3-hydroxypropyl]amino]-2-hydroxypropyl]azetidine-2-carboxylic acid
N-(3-(3-carboxypropylamino)-2-hydroxy-3-carboxypropyl)azetidine-2-carboxylic acid
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Articles:
PubMed: [Bioinorganic Chemistry of Iron].
PubMed: The iron-chelate transporter OsYSL9 plays a role in iron distribution in developing rice grains.
PubMed: Characterisation of the nicotianamine aminotransferase and deoxymugineic acid synthase genes essential to Strategy II iron uptake in bread wheat (Triticum aestivum L.).
PubMed: Diurnal Changes in Transcript and Metabolite Levels during the Iron Deficiency Response of Rice.
PubMed: Comparison on cellular mechanisms of iron and cadmium accumulation in rice: prospects for cultivating Fe-rich but Cd-free rice.
PubMed: Identification and molecular characterization of the nicotianamine synthase gene family in bread wheat.
PubMed: Mugineic acid, active ingredient of wheat grass: an oral novel hexadentate iron chelator in iron overloaded diseases.
PubMed: Evolutionary analysis of iron (Fe) acquisition system in Marchantia polymorpha.
PubMed: Transcriptomic analyses of maize ys1 and ys3 mutants reveal maize iron homeostasis.
PubMed: The Phytosiderophore Efflux Transporter TOM2 Is Involved in Metal Transport in Rice.
PubMed: Iron deficiency responses in rice roots.
PubMed: Synthesis of [13C4]-labeled 2'-deoxymugineic acid.
PubMed: Rice nicotianamine synthase localizes to particular vesicles for proper function.
PubMed: Iron biofortification of rice using different transgenic approaches.
PubMed: Rice genes involved in phytosiderophore biosynthesis are synchronously regulated during the early stages of iron deficiency in roots.
PubMed: Nicotianamine synthase 2 localizes to the vesicles of iron-deficient rice roots, and its mutation in the YXXφ or LL motif causes the disruption of vesicle formation or movement in rice.
PubMed: Iron-biofortification in rice by the introduction of three barley genes participated in mugineic acid biosynthesis with soybean ferritin gene.
PubMed: Characterizing the crucial components of iron homeostasis in the maize mutants ys1 and ys3.
PubMed: A sensitive LC-ESI-Q-TOF-MS method reveals novel phytosiderophores and phytosiderophore-iron complexes in barley.
PubMed: OsYSL16 plays a role in the allocation of iron.
PubMed: Getting a sense for signals: regulation of the plant iron deficiency response.
PubMed: Analysis of iron-phytosiderophore complexes in soil related samples: LC-ESI-MS/MS versus CE-MS.
PubMed: OsYSL6 is involved in the detoxification of excess manganese in rice.
PubMed: A novel barley yellow stripe 1-like transporter (HvYSL2) localized to the root endodermis transports metal-phytosiderophore complexes.
PubMed: The binding of aluminum to mugineic acid and related compounds as studied by potentiometric titration.
PubMed: Isolation and characterization of a barley yellow stripe-like gene, HvYSL5.
PubMed: Mugineic acid derivatives as molecular probes for the mechanistic elucidation of iron acquisition in barley.
PubMed: Recent insights into iron homeostasis and their application in graminaceous crops.
PubMed: Successful reproduction requires the function of Arabidopsis Yellow Stripe-Like1 and Yellow Stripe-Like3 metal-nicotianamine transporters in both vegetative and reproductive structures.
PubMed: Toward mechanistic elucidation of iron acquisition in barley: efficient synthesis of mugineic acids and their transport activities.
PubMed: Complexation of metals by phytosiderophores revealed by CE-ESI-MS and CE-ICP-MS.
PubMed: Time course analysis of gene expression over 24 hours in Fe-deficient barley roots.
PubMed: Rice OsYSL15 is an iron-regulated iron(III)-deoxymugineic acid transporter expressed in the roots and is essential for iron uptake in early growth of the seedlings.
PubMed: Investigation of ascorbate-mediated iron release from ferric phytosiderophores in the presence of nicotianamine.
PubMed: Deoxymugineic acid increases Zn translocation in Zn-deficient rice plants.
PubMed: Identification and localisation of the rice nicotianamine aminotransferase gene OsNAAT1 expression suggests the site of phytosiderophore synthesis in rice.
PubMed: Isotopomer-based metabolomic analysis by NMR and mass spectrometry.
PubMed: Mutation in nicotianamine aminotransferase stimulated the Fe(II) acquisition system and led to iron accumulation in rice.
PubMed: CE of phytosiderophores and related metal species in plants.
PubMed: A practical synthesis of the phytosiderophore 2'-deoxymugineic acid: a key to the mechanistic study of iron acquisition by graminaceous plants.
PubMed: [Responses to iron-deficiency stress by graminaceous plants].
PubMed: The rice bHLH protein OsIRO2 is an essential regulator of the genes involved in Fe uptake under Fe-deficient conditions.
PubMed: Promoter analysis of iron-deficiency-inducible barley IDS3 gene in Arabidopsis and tobacco plants.
PubMed: Transporters of ligands for essential metal ions in plants.
PubMed: The expression of iron homeostasis-related genes during rice germination.
PubMed: Deoxymugineic Acid synthase: a gene important for fe-acquisition and homeostasis.
PubMed: Separation and identification of phytosiderophores and their metal complexes in plants by zwitterionic hydrophilic interaction liquid chromatography coupled to electrospray ionization mass spectrometry.
PubMed: Biosynthesis and secretion of mugineic acid family phytosiderophores in zinc-deficient barley.
PubMed: Cloning and characterization of deoxymugineic acid synthase genes from graminaceous plants.
PubMed: Anion exchange liquid chromatography--inductively coupled plasma-mass spectrometry detection of the Co2+, Cu2+, Fe3+ and Ni2+ complexes of mugineic and deoxymugineic acid.
PubMed: [Study on the structure activity relationship of a phytosiderophore, mugineic acid].
PubMed: A specific transporter for iron(III)-phytosiderophore in barley roots.
PubMed: Mg-dechelation activity in radish cotyledons with artificial and native substrates, Mg-chlorophyllin a and chlorophyllide a.
PubMed: Expression of iron-acquisition-related genes in iron-deficient rice is co-ordinately induced by partially conserved iron-deficiency-responsive elements.
PubMed: Yellow stripe1. Expanded roles for the maize iron-phytosiderophore transporter.
PubMed: Three nicotianamine synthase genes isolated from maize are differentially regulated by iron nutritional status.
PubMed: Speciation of iron coordinated by phytosiderophores by use of HPLC with pulsed amperometric detection and AAS.
PubMed: cDNA microarray analysis of gene expression during Fe-deficiency stress in barley suggests that polar transport of vesicles is implicated in phytosiderophore secretion in Fe-deficient barley roots.
PubMed: Real-time [11C]methionine translocation in barley in relation to mugineic acid phytosiderophore biosynthesis.
PubMed: Determination of phytosiderophores by anion-exchange chromatography with pulsed amperometric detection.
PubMed: The expression of a barley HvNAS1 nicotianamine synthase gene promoter-gus fusion gene in transgenic tobacco is induced by Fe-deficiency in roots.
PubMed: In vivo evidence that Ids3 from Hordeum vulgare encodes a dioxygenase that converts 2'-deoxymugineic acid to mugineic acid in transgenic rice.
PubMed: Nicotianamine synthase gene expression differs in barley and rice under Fe-deficient conditions.
PubMed: Two dioxygenase genes, Ids3 and Ids2, from Hordeum vulgare are involved in the biosynthesis of mugineic acid family phytosiderophores.
PubMed: Hydroxylated phytosiderophore species possess an enhanced chelate stability and affinity for iron(III).
PubMed: Induced activity of adenine phosphoribosyltransferase (APRT) in iron-deficiency barley roots: a possible role for phytosiderophore production.
PubMed: A formal asymmetric synthesis of Mugineic acid: an efficient synthetic route through chiral oxazolidinone.
PubMed: Cloning two genes for nicotianamine aminotransferase, a critical enzyme in iron acquisition (Strategy II) in graminaceous plants.
PubMed: Cloning of nicotianamine synthase genes, novel genes involved in the biosynthesis of phytosiderophores.
PubMed: Expression cloning in Fe2+ transport defective yeast of a novel maize MYC transcription factor.
PubMed: Characterization of Fe(III)-deferoxamine and Mn(II)-pectin as magnetic resonance imaging contrast agents.
PubMed: Comprehensive analysis of organic ligands in whole root exudates using nuclear magnetic resonance and gas chromatography-mass spectrometry.
PubMed: Isolation of nicotianamine as a gelatinase inhibitor.
PubMed: Incorporation of15N and14C of methionine into the mugineic acid family of phytosiderophores in iron-deficient barley roots.
PubMed: Two Related Biosynthetic Pathways of Mugineic Acids in Gramineous Plants.
PubMed: Expression of a gene specific for iron deficiency (Ids3) in the roots of Hordeum vulgare.
PubMed: Indirect utilization of the phytosiderophore mugineic acid as an iron source to rhizosphere fluorescent Pseudomonas.
PubMed: Short-term effects of rhizosphere microorganisms on fe uptake from microbial siderophores by maize and oat.
PubMed: Biosynthesis of Phytosiderophores : In Vitro Biosynthesis of 2'-Deoxymugineic Acid from l-Methionine and Nicotianamine.
PubMed: Mugineic acid: non-selective enhancement of excitatory amino acid actions on rat central neurones.
PubMed: Separation and determination of mugineic acid and its analogues by high-performance liquid chromatography.
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