[ CAS No. 328-50-7 ] {[proInfo.proName]}

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2D 3D

Structure of 328-50-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 328-50-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 328-50-7 ]

SDS Specification

Alternatived Products of [ 328-50-7 ]

Product Details of [ 328-50-7 ]

CAS No. :	328-50-7	MDL No. :	MFCD00004165
Formula :	C₅H₆O₅	Boiling Point :	-
Linear Structure Formula :	HOOCCOCH₂CH₂COOH	InChI Key :	KPGXRSRHYNQIFN-UHFFFAOYSA-N
M.W :	146.10	Pubchem ID :	51
Synonyms :	Alpha-Ketoglutaric acid;α-Ketoglutaric Acid;NSC 17391;α-KGA;2-oxoglutaric acid;alpha-ketoglutarate	Chemical Name :	2-Oxopentanedioic acid

Calculated chemistry of [ 328-50-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.4
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	2.0
Molar Refractivity :	29.89
TPSA :	91.67 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-0.09
Log Po/w (XLOGP3) :	-0.9
Log Po/w (WLOGP) :	-0.5
Log Po/w (MLOGP) :	-1.06
Log Po/w (SILICOS-IT) :	-0.62
Consensus Log Po/w :	-0.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	0.09
Solubility :	178.0 mg/ml ; 1.22 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.54
Solubility :	41.9 mg/ml ; 0.287 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.64
Solubility :	632.0 mg/ml ; 4.33 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 328-50-7 ]

Signal Word:	Danger	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338+P310	UN#:	N/A
Hazard Statements:	H318	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 328-50-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 328-50-7 ]
Downstream synthetic route of [ 328-50-7 ]

[ 328-50-7 ] Synthesis Path-Upstream 1~1

1
[ 328-50-7 ]
[ 1927-25-9 ]
[ 6027-21-0 ]
[ 6893-26-1 ]
[ 56-86-0 ]

Reference： [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 17, p. 3505 - 3509

[ 328-50-7 ] Synthesis Path-Downstream 1~7

1
[ 328-50-7 ]
[ 56291-51-1 ]
[ 156095-50-0 ]

Reference： [1]Il Farmaco,1994,vol. 49,p. 259 - 265

2
[ 328-50-7 ]
[ 69134-53-8 ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 2713 - 2728
[2]Journal of the Brazilian Chemical Society,2019,vol. 30,p. 149 - 157

3
[ 328-50-7 ]
3,4-dihydroxy-phenethylamine hydrochloride [ No CAS ]
[ 69134-53-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1986,vol. 25,p. 1176 - 1178

4
[ 328-50-7 ]
[ 68-04-2 ]
[ 54897-59-5 ]
[ 107-15-3 ]
[ 127689-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ATP; magnesium chloride; N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid;SbnC (NIS synthetase); SbnE (NIS synthetase); SbnF (NIS synthetase); In water; at 20℃;pH 7.4;In the dark;	In Vitro Synthesis of Staphyloferrin BBioinformatic analyses of the predicted protein products from the staphyloferrin B biosynthesis operon identified three enzymes (SbnC, SbnE and SbnF) that belong to the NIS family of siderophore synthetase enzymes. These enzymes are thought to catalyze the ATP and Mg2+-dependent activation of carboxylate substrates, in a reaction that proceeds through an acyl-adenlyate intermediate that is then recognized by an amine substrate to yield an overall condensation reaction to an amide. To examine the activity of the SbnC, SbnE and SbnF enzymes, and to determine their role in staphyloferrin B synthesis, each was independently overexpressed in E. coli as a hexahistidine-tagged derivative, and subsequently purified using nickel-affinity chromatography. When the three synthetases were incubated together with staphyloferrin B components L-2,3-diaminopropionic acid (Dap), citrate, 1,2-diaminoethane (Dae), and alpha-ketoglutarate (alpha-KG), an ion corresponding to staphyloferrin B was not formed. Additional purified Sbn enzymes were added to the reaction. Notably, when SbnH, a putative PLP-dependent decarboxylase, was combined in reactions with the three synthetases and substrates, an ion corresponding to that of staphyloferrin B was produced. The staphyloferrin B ion was not produced when any of ATP, Mg2+, SbnC, SbnE, SbnF, SbnH, Dap, citrate or alpha-KG was omitted from the reaction (data not shown). Notably, staphyloferrin B synthesis could proceed without the addition of Dae in the reaction. ESI-MS/MS was used to confirm that staphyloferrin B produced in vitro was the same as that isolated from spent culture supernatants of iron-starved S. aureus.

Reference： [1]Patent: US2011/245321,2011,A1 .Location in patent: Page/Page column 13-14

5
[ 328-50-7 ]
[ 21495-41-0 ]
[ 56-86-0 ]
[ 1138220-65-1 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 12105 - 12108

6
[ 328-50-7 ]
[ 65202-50-8 ]

Reference： [1]Patent: EP3333157,2018,A1

7
[ 6972-82-3 ]
[ 328-50-7 ]
3-(1-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropteridin-6-yl)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With acetic acid; for 1h;Reflux;	A suspension of <strong>[6972-82-3]5,6-diamino-1-methyluracil</strong> (1) (1.56 g, 10 mmol) in AcOH (30 ml) was treated with 2-oxopentanedioic acid (1.46 g, 10 mmol). The reaction mixture was heated, giving a clear solution from which a precipitate formed. The reaction mixture was refluxed for 1 h and cooled. The obtained precipitate was filtered off, washed with water, and dried. Yield 1.99 g(75percent), light-yellow powder, mp >300°. IR spectrum,nu, cm?1: 3500, 3056, 2980, 1643, 1556, 1452, 1421, 1325,1181, 834, 791, 750, 693, 669, 630. 1H NMR spectrum,delta, ppm (J, Hz): 2.69 (2H, t, J = 7.2, CH2CH2COOH); 2.93(2H, t, J = 7.1, CH2CH2COOH); 3.44 (3H, s, 1-NCH3);11.42 (1H, s, 3-NH); 11.57?11.98 (2H, m, 8-NH, COOH).13C NMR spectrum, delta, ppm: 26.9 (CH2CH2COOH); 28.5(NCH3); 30.7 (CH2CH2COOH); 118.2 (C-4a); 141.2(C-8a); 148.1 (C-6); 150.6 (C-2); 159.9 (C-4,7); 174.1(COOH). Mass spectrum (EI), m/z (Irel, percent): 248 (29), 246(9), 221 (11), 220 (100), 167 (18), 149 (28), 121 (7), 83(19), 68 (7), 67 (7). Mass spectrum (APCI-ESI), m/z (Irel, percent):267 [M+]+ (100). Found, percent: C 45.15; H 3.82; N 21.09.C10H10N4O5. Calculated, percent: C 45.12; H 3.79; N 21.05.

Reference： [1]Chemistry of Heterocyclic Compounds,2019,vol. 55,p. 408 - 415
Khim. Geterotsikl. Soedin.,2019,vol. 55,p. 408 - 415,8

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Technical Information

? Arndt-Eistert Homologation ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hunsdiecker-Borodin Reaction ? Hydride Reductions ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Preparation of Carboxylic Acids ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Carboxylic Acids ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P231	Handle under inert gas.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
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Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
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P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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H200	Unstable explosive
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 328-50-7 ] {[proInfo.proName]}

Quality Control of [ 328-50-7 ]

Related Doc. of [ 328-50-7 ]

Product Details of [ 328-50-7 ]

Calculated chemistry of [ 328-50-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 328-50-7 ]

Application In Synthesis of [ 328-50-7 ]

[ 328-50-7 ] Synthesis Path-Upstream 1~1

[ 328-50-7 ] Synthesis Path-Downstream 1~7

Technical Information

Similar Product of [ 328-50-7 ]

Related Functional Groups of [ 328-50-7 ]

Ketones

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Similar Product of
[ 328-50-7 ]

Related Functional Groups of
[ 328-50-7 ]