[ CAS No. 541-15-1 ] {[proInfo.proName]}

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Quality Control of [ 541-15-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 541-15-1 ]

SDS Specification

Alternatived Products of [ 541-15-1 ]

Product Citations

Age and APOE affect L-carnitine system metabolites in the brain in the APOE-TR model

Huguenard, Claire J. C. ; Cseresznye, Adam ; Darcey, Teresa , et al. Front. Aging Neurosci.,2023,14,1059017. DOI: 10.3389/fnagi.2022.1059017 PubMed ID: 36688151

Abstract: With age the apolipoprotein E (APOE) E4 allele (involved in lipid homeostasis) is associated with perturbation of bioenergetics pathways in Alzheimer's disease (AD). We therefore hypothesized that in aging mice APOE genotype would affect the L-carnitine system (central to lipid bioenergetics), in the brain and in the periphery. Using liquid chromatog.-mass spectrometry, levels of L-carnitine and associated metabolites: γ-butyrobetaine (GBB), crotonobetaine, as well as acylcarnitines, were evaluated at 10-, 25-, and 50-wk, in the brain and the periphery, in a targeted replacement mouse model of human APOE (APOE-TR). Aged APOE-TR mice were also orally administered 125 mg/kg of L-carnitine daily for 7 days followed by evaluation of brain, liver, and plasma L-carnitine system metabolites. Compared to E4-TR, an age-dependent increase among E2- and E3-TR mice was detected for medium- and long-chain acylcarnitines (MCA and LCA, resp.) within the cerebrovasculature and brain parenchyma. While following L-carnitine oral challenge, E4-TR mice had higher increases in the L-carnitine metabolites, GBB and crotonobetaine in the brain and a reduction of plasma to brain total acylcarnitine ratios compared to other genotypes. These studies suggest that with aging, the presence of the E4 allele may contribute to alterations in the L-carnitine bioenergetic system and to the generation of L-carnitine metabolites that could have detrimental effects on the vascular system. Collectively the E4 allele and aging may therefore contribute to AD pathogenesis through aging-related lipid bioenergetics as well as cerebrovascular dysfunctions.

Keywords: apolipoproteins ; fatty acid metabolism ; lipid oxidation ; vascular biology ; Alzheimer's disease

Purchased from AmBeed: 541-15-1

Product Details of [ 541-15-1 ]

CAS No. :	541-15-1	MDL No. :	MFCD00038747
Formula :	C₇H₁₅NO₃	Boiling Point :	-
Linear Structure Formula :	(CH₃)₃NCH₂CH(OH)CH₂COO	InChI Key :	PHIQHXFUZVPYII-ZCFIWIBFSA-N
M.W :	161.20	Pubchem ID :	10917
Synonyms :	(R)-Carnitine;Levocarnitine;Carnitine;ST-198;L-Cartin;Carnitor;R-Carnitine;(–)-Carnitine	Chemical Name :	(R)-3-Hydroxy-4-(trimethylammonio)butanoate

Calculated chemistry of [ 541-15-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.13
TPSA :	60.36 ?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) :	-7.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-2.37
Log Po/w (XLOGP3) :	-0.84
Log Po/w (WLOGP) :	-1.81
Log Po/w (MLOGP) :	-3.79
Log Po/w (SILICOS-IT) :	-0.8
Consensus Log Po/w :	-1.92

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.05
Solubility :	145.0 mg/ml ; 0.899 mol/l
Class :	Very soluble
Log S (Ali) :	0.05
Solubility :	182.0 mg/ml ; 1.13 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.74
Solubility :	29.1 mg/ml ; 0.18 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 541-15-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 541-15-1 ]

* 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 [ 541-15-1 ]
Downstream synthetic route of [ 541-15-1 ]

[ 541-15-1 ] Synthesis Path-Upstream 1~1

1
[ 541-15-1 ]
[ 6645-46-1 ]

Reference： [1] Patent: WO2017/195031, 2017, A1, . Location in patent: Page/Page column 12; 13

[ 541-15-1 ] Synthesis Path-Downstream 1~3

1
[ 6168-83-8 ]
[ 541-15-1 ]
(S)-3'-hydroxybutanoyl-(R)-carnitine [ No CAS ]

Reference： [1]Phytochemistry,2006,vol. 67,p. 2676 - 2680

2
[ 6645-46-1 ]
[ 541-15-1 ]

Reference： [1]Chinese Chemical Letters,2011,vol. 22,p. 765 - 767
[2]Patent: WO2018/226841,2018,A1

3
[ 541-15-1 ]
[ 6645-46-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 55 - 60℃;	bOg of L-carnitine is dried in a vacuum oven at 80 - 90 C for 2-3 days or in a phosphorous pentoxide chamber for 5 -7 days. Once dry the material is weighed and a slurry is created at 1 g/mL in deionized water. One molar equivalent of concentrated HCI is added and the solid is dissolved. The solution is heated on a hotplate open at 55 - 60 C in a shallow container for 5 - 8 hours until very viscous and then placed in an oven at the same temperature for 12-16 hours until a stiff layer exists or nucleation is visible. The material is then further dried with a vacuum oven at 80 - 90 C for 2- 3 days until the solid is opaque white and easily flaking off the container. The particulate material was gathered and stored in a desiccator with phosphorus pentoxide for subsequent analysis. The material was characterized by proton NMR, 500 MHz, Methanol, 6 2.57 (dd, 1H); 3.25 (s, 9H); 3.48 (m, 3H); 4.58 (m, 1H).

Reference： [1]Patent: WO2017/195031,2017,A1 .Location in patent: Page/Page column 12; 13

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Isomers

Technical Information

? Acyl Group Substitution ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents

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Precautionary Statements-General
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P211	Do not spray on an open flame or other ignition source.
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.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P250	Do not subject to grinding/shock/friction.
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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.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
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.
Response
Code	Phrase
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P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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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.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
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
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
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.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
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:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
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P406	Store in corrosive resistant/ container with a resistant inner liner.
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P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H271	May cause fire or explosion; strong oxidizer
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H301	Toxic if swallowed
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[ CAS No. 541-15-1 ] {[proInfo.proName]}

Quality Control of [ 541-15-1 ]

Related Doc. of [ 541-15-1 ]

Product Citations

Product Details of [ 541-15-1 ]

Calculated chemistry of [ 541-15-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 541-15-1 ]

Application In Synthesis of [ 541-15-1 ]

[ 541-15-1 ] Synthesis Path-Upstream 1~1

[ 541-15-1 ] Synthesis Path-Downstream 1~3

Technical Information

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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