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A6706

O-Acetyl-L-carnitine hydrochloride

≥99% (titration)

Synonym(s):

Acetyl L-carnitine HCl, (R)-3-Acetoxy-4-(trimethylammonio)butyrate hydrochloride, ALC, ALCAR, R-(−)-2-Acetyloxy-3-carboxy-N,N,N-trimethyl-1-propanaminium chloride

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About This Item

Empirical Formula (Hill Notation):
C9H17NO4 · HCl
CAS Number:
5080-50-2
Molecular Weight:
239.70
NACRES:
NA.83
PubChem Substance ID:
24891132
UNSPSC Code:
12352204
MDL number:
MFCD00082230
Beilstein/REAXYS Number:
4340103
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Product Name

O-Acetyl-L-carnitine hydrochloride, ≥99% (titration), powder

biological source

synthetic

Quality Level

300

assay

≥99% (titration)

form

powder

optical activity

[α]25/D −28°, c = 2 in H2O(lit.)

color

white to off-white

mp

194 °C

solubility

H2O: 100 mg/mL

application(s)

cell analysis

storage temp.

2-8°C

SMILES string

C[N+](C)(C)C[C@H](OC(C)=O)CC(O)=O.[Cl-]

InChI

1S/C9H17NO4.ClH/c1-7(11)14-8(5-9(12)13)6-10(2,3)4;/h8H,5-6H2,1-4H3;1H/t8-;/m1./s1

InChI key

JATPLOXBFFRHDN-DDWIOCJRSA-N

General description

Acetyl-L-carnitine (ALC/ALCAR), a quasi-vitamin is a metabolite of carnitine, present in mammalian plasma and tissues. It is the acetylated form of L-carnitine (LC). ALCAR is used as a dietary supplement. It is present at high level in the hypothalamus.

Application

O-Acetyl-L-carnitine hydrochloride has been used:
  • as a bioactive compound to study its effect on the proliferation of B-lymphoblastoid cell lines (BLCL) and its immune modulating properties on influenza virus specific human B and T cell responses in vitro[1]
  • as in vitro maturation (IVM) media component to study its effects on lamb oocyte blastocyst rate, ultrastructure and mitochondrial DNA copy number
  • as a metabolite/chemical standard to quantify the metabolite levels in murine tumor interstitial fluid

Biochem/physiol Actions

Endogenous mitochondrial metabolite that transports acetyl groups across the mitochondrial membrane.
Endogenous mitochondrial metabolite that transports acetyl groups across the mitochondrial membrane. Exogenous acetylcarnitine enhances mitochondrial function in aged rats. As an acetate donor to coenzyme A, it increases the central and peripheral acetylcholine synthesis and function. Acetylcarnitine has antinociceptive activity that may be mediated by enhanced activity of muscarinic cholinergic receptors or mGlu2 glutamate receptors.
Acetyl L-carnitine (ALC) plays a vital role in intermediary metabolism and in improving female fertility. The oxidative and metabolic status of the female reproductive system is controlled by ALC. ALC possesses cholinomimetic and anti-inflammatory effects. It controls γ-amino butyric acid (GABA) system. ALC is capable of modifying the rate of glucose usage in the brain. It also possesses a neuroprotective role in the developing brain.

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1 of 1

This Item
A15099210742602
O-Acetyl-L-carnitine hydrochloride ≥99% (titration), powder

Sigma-Aldrich

A6706

O-Acetyl-L-carnitine hydrochloride

Acetyl-DL-carnitine hydrochloride

Sigma-Aldrich

A1509

Acetyl-DL-carnitine hydrochloride

O-Acetyl-L-carnitine hydrochloride analytical standard

Supelco

92107

O-Acetyl-L-carnitine hydrochloride

Propionyl-L-carnitine ≥94.0% (HPLC)

Sigma-Aldrich

42602

Propionyl-L-carnitine

form

powder

form

powder

form

powder or crystals

form

powder or crystals

assay

≥99% (titration)

assay

>98% (TLC)

assay

≥96.0% (HPLC), 96.0-104.0% (AT)

assay

≥94.0% (HPLC)

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

optical activity

[α]25/D −28°, c = 2 in H2O(lit.)

optical activity

-

optical activity

[α]/D -27.0±2.0°, c = 1 in H2O

optical activity

[α]/D -23±3°, c = 1 in H2O

solubility

H2O: 100 mg/mL

solubility

-

solubility

-

solubility

-

mp

194 °C

mp

-

mp

-

mp

-

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pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000533256
0000533257
0000533257
0000533256
0000495240

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Rosa Palmeri et al.
Foods (Basel, Switzerland), 9(2) (2020-02-27)
Consumer interest toward natural ingredients is creating a growing trend in the food industry and research for the development of natural products such as colorants, antimicrobials and antioxidants. Semi-processed frozen prickly pear (Opuntia ficus-indica (L.) Mill.) juices (PPJs), obtained from
Abbi D Lane-Cordova et al.
PloS one, 12(10), e0186495-e0186495 (2017-10-20)
Having experienced 2-3 births is associated with reduced mortality versus women with <2 or ≥4 births. The effect of 2-3 births on lifespan may be associated with delayed cellular aging. We hypothesized telomere length, a marker of cellular aging, would
Kifayatullah Shah et al.
Drug delivery, 24(1), 1631-1647 (2017-10-25)
The study investigated aerosolization, pulmonary inhalation, intracellular trafficking potential in macrophages and pharmacokinetics profiles of rifampicin-oleic acid first-generation nanoemulsion and its respective chitosan- and chitosan-folate conjugate-decorated second and third-generation nanoemulsions, delivered via nebulization technique. The nanoemulsions were prepared by conjugate
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Global Trade Item Number

SKUGTIN
A6706-1G04061833382745
A6706-5G04061832421186

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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