[ CAS No. 69-72-7 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 69-72-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 69-72-7 ]

SDS Specification

Alternatived Products of [ 69-72-7 ]

Product Citations

Polyfluorinated salicylic acid analogs do not interfere with siderophore biosynthesis

Hegde, Pooja ; Orimoloye, Moyosore O. ; Sharma, Sachin , et al. Tuberculosis,2023,140,102346. DOI: 10.1016/j.tube.2023.102346 PubMed ID: 37119793

Abstract: Tuberculosis (TB), caused by Mycobacterium tuberculosis (Mtb) is a leading cause of infectious disease mortality. The salicylic acid derived small mol. siderophores known as mycobactins are essential in vivo for iron acquisition of Mtb where iron is restricted in the host. Herein, we synthesize and explore the mechanism of action of polyfluorinated salicylic acid derivates, which were previously reported to possess potent antimycobacterial activity. We hypothesized fluorinated salicylic acid derivates may inhibit mycobactin biosynthesis through initial bioactivation and conversion to downstream metabolites that block late steps in assembly of the mycobactins. Enzymic studies demonstrated that some of the fluorinated salicylic acid derivatives compounds were readily activated by the bifunctional adenylating enzyme MbtA, responsible for incorporation of salicylic acid into the mycobactin biosynthetic pathway; however, they did not inhibit mycobactin biosynthesis as confirmed by LS-MS/MS using an authentic synthetic mycobactin standard Further mechanistic anal. of the most active derivative (Sal-4) using an MbtA-overexpressing Mtb strain as well as complementation studies with iron and salicylic acid revealed Sal-4 cannot be antagonized by overexpression of MbtA or through supplementation with iron or salicylic acid. Taken together, our results indicate the observed antimycobacterial activity of polyfluorinated salicylic acid derivative is independent of mycobactin biosynthesis.

Purchased from AmBeed: 69-72-7

Product Details of [ 69-72-7 ]

CAS No. :	69-72-7	MDL No. :	MFCD00002439
Formula :	C₇H₆O₃	Boiling Point :	-
Linear Structure Formula :	C₆H₄(OH)(CO₂H)	InChI Key :	YGSDEFSMJLZEOE-UHFFFAOYSA-N
M.W :	138.12	Pubchem ID :	338
Synonyms :	2-Hydroxybenzoic Acid	Chemical Name :	2-Hydroxybenzoic acid

Calculated chemistry of [ 69-72-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	35.42
TPSA :	57.53 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.13
Log Po/w (XLOGP3) :	2.26
Log Po/w (WLOGP) :	1.09
Log Po/w (MLOGP) :	0.99
Log Po/w (SILICOS-IT) :	0.74
Consensus Log Po/w :	1.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.5
Solubility :	0.439 mg/ml ; 0.00318 mol/l
Class :	Soluble
Log S (Ali) :	-3.1
Solubility :	0.109 mg/ml ; 0.000786 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.17
Solubility :	9.4 mg/ml ; 0.0681 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 69-72-7 ]

Signal Word:	Danger	Class:	N/A
Precautionary Statements:	P201-P202-P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P308+P313-P405-P501	UN#:	N/A
Hazard Statements:	H302-H318-H361	Packing Group:	N/A
GHS Pictogram:

Applications of [ 69-72-7 ]

Salicylic acid (CAS: 69-72-7) can be used in the preparation of Sulfasalazine (Azulfidine) (CAS: 599-79-1). Sulfasalazine is indicated for managing inflammatory diseases such as ulcerative colitis and rheumatoid arthritis (RA).

Application In Synthesis of [ 69-72-7 ]

* 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 [ 69-72-7 ]
Downstream synthetic route of [ 69-72-7 ]

[ 69-72-7 ] Synthesis Path-Upstream 1~2

1
[ 357657-22-8 ]
[ 56-87-1 ]
[ 692-04-6 ]
[ 1946-82-3 ]
[ 35436-74-9 ]
[ 69-72-7 ]
[ 50-78-2 ]

Reference： [1] Archiv der Pharmazie, 1985, vol. 318, # 2, p. 120 - 127

2
[ 56-87-1 ]
[ 50-78-2 ]
[ 692-04-6 ]
[ 1946-82-3 ]
[ 357657-22-8 ]
[ 35436-74-9 ]
[ 69-72-7 ]

Reference： [1] Archiv der Pharmazie, 1985, vol. 318, # 2, p. 120 - 127

[ 69-72-7 ] Synthesis Path-Downstream 1~4

1
[ 69-72-7 ]
[ 255735-88-7 ]
[ 1204318-26-2 ]

Yield	Reaction Conditions	Operation in experiment
40%	With 1H-imidazole; dicyclohexyl-carbodiimide; In ethyl acetate; at 0 - 20℃;	To a solution of tert-butyl 2-aminopropylcarbamate (3.6 g, 20.6 mmol), 2-hydroxybenzoic acid (2.79 g, 20.6 mmol) and imidazole (1.41 g, 20.6 mmol) in EtOAc (100 mL) at 0° C. was slowly added a solution of DCC (4.26 g, 20.6 mmol) in EtOAc (50 mL). The reaction mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography, EtOAc/Petroleum ether (0-20percent) to afford tert-butyl 2-(2-hydroxybenzamido)propylcarbamate (2.4 g, 40percent) as a white solid.

Reference： [1]Patent: US2010/41748,2010,A1 .Location in patent: Page/Page column 122

2
[ 119072-54-7 ]
[ 5779-93-1 ]
[ 69-72-7 ]
[ 1310409-69-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2991 - 2997

3
[ 29390-67-8 ]
[ 69-72-7 ]
6^A-deoxy-6^A-((2-hydroxybenzoyl)amino)-β-cyclodextrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		6A-Deoxy-6A-((2-hydroxybenzoyl)amino)-beta-cyclodextrin. The synthesis was adapted from apreviously published method.15 Solutions of N,N'-dicyclohexylcarbodiimide (91 mg, 0.44 mmol)in DMF (4 mL) and hydroxybenzotriazole (68 mg, 0.44 mmol) in DMF (4 ml) were added to asolution of salicylic acid (61 mg, 0.44 mmol) in DMF (5 mL) cooled to 0 oC. The reactionmixture was stirred for 0.5 hours at 0 oC and a solution of 6A-deoxy-6A-amino- -cyclodextrin16,17 (500 mg, 0.44 mmol) in DMF (17 mL) was added dropwise. The reactionmixture was then stirred for another hour at 0 oC and 48 hours at room temperature. The reactionwas quenched by pouring the mixture into acetone (300 mL). The precipitate was filtered out andpurified by crystallization from water to yield 333 mg (60percent) of the title compound as a whitepowder. Mp 228 oC (decomp.). IR (KBr): 3507, 3280, 3155, 3117, 3058, 1642, 1150, 1030 cm-1.1H NMR (DMSO-d6): 12.39 (s, 1 H, Ar-OH), 8.67 (s, 1 H, -NH-), 7.82 (d, J 7.6 Hz, 1 H, Ar-H), 7.38 (t, J 7.7 Hz, 1H, Ar-H), 6.94?6.82 (m, 2 H,Ar-H), 5.94?5.51 (m, 14 H, 7 x CD-OH (2),7 x CD-OH (3)), 4.95?4.75 (m, 7 H, 7 x CD-H (1)), 4.56?4.33 (m, 6 H, 6 x CD-OH (6)), 3.92-3.10 (m, 42 H, 7 x CD-H (2), 7 x CD-H (3), 7 x CD-H (4), 7 x CD-H (5), 14 x CD-H (6)) ppm.13C NMR (DMSO-d6): = 168.61 (-CONH-), 159.65 (Ar-C-OH),133.52(Ar-C), 128.15(Ar-C),118.51(Ar-C), 117.21(Ar-C), 115.56(Ar-C), 102.39?101.88 (7 x CD-C (1)), 84.16?59.91 (7xCDC(2), 7 x CD-C (3), 7 x CD-C (4), 7 x CD-C (5), 7 x CD-C (6)) ppm.

Reference： [1]Arkivoc,2016,vol. 2016,p. 249 - 267

4
[ 30465-68-0 ]
[ 69-72-7 ]
2-hydroxy-N-(5-methoxyquinolin-8-yl)-6-(trifluoromethylthio)benzamide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 6167 - 6175

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Historical Records

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[ 69-72-7 ]

A1373046[ 78646-09-0 ]

2-Hydroxybenzoic-carboxy-13C acid

Reason: Stable Isotope

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Response
Code	Phrase
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P310	Immediately call a POISON CENTER or doctor/physician.
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P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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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.
P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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H202	Explosive; severe projection hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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[ CAS No. 69-72-7 ] {[proInfo.proName]}

Quality Control of [ 69-72-7 ]

Related Doc. of [ 69-72-7 ]

Product Citations

Product Details of [ 69-72-7 ]

Calculated chemistry of [ 69-72-7 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 69-72-7 ]

Applications of [ 69-72-7 ]

Application In Synthesis of [ 69-72-7 ]

[ 69-72-7 ] Synthesis Path-Upstream 1~2

[ 69-72-7 ] Synthesis Path-Downstream 1~4

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