Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].

Absorption, Distribution and Excretion
Following ingestion of a 2.0 g/kg dose of cetyl alcohol in rats, partial absorption was observed. Gavage administration of 0.2 mg cetyl alcohol via gastric tube to rats showed good absorption, with 63-96% of the radiolabeled cetyl alcohol detected in lymph. Approximately 15% of the cetyl alcohol remained unchanged as it passed through the small intestinal mucosal cells, but most was oxidized to palmitic acid. The absorption rate in poultry has been reported to be 26%. Following ingestion of a 2.0 g/kg dose in rats, approximately 20% of the dose was excreted in feces as unchanged molecules. This is likely due to the interconversion of fatty acids and alcohols, leading to the conversion of palmitic acid to cetyl alcohol as it passes through the intestinal mucosal cells into the intestinal lumen. In rats, cetyl alcohol is also excreted in urine as conjugated glucuronic acid and exhaled carbon dioxide. Following ingestion of a 2.0 g/kg body weight dose in rats, 1-hexadecane was partially absorbed and metabolized, with approximately 20% excreted unchanged in feces.

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Metabolism/Metabolites
In rats, cetyl alcohol is partially metabolized to palmitic acid after ingestion of a 2.0 g/kg dose. After administration of 0.2 mg cetyl alcohol via gastric tube to rats, most of the cetyl alcohol is oxidized to palmitic acid as it passes through the small intestinal mucosal cells and is incorporated into triglycerides and phospholipids.
Cetyl alcohol is oxidized to the corresponding fatty acid, palmitic acid, in rats.
Primary fatty alcohols undergo two main reactions in vivo: oxidation to carboxylic acids and direct conjugation with glucuronic acid. The first reaction generates an intermediate aldehyde, from which the carboxylic acid may be completely oxidized to carbon dioxide, excreted as carbon dioxide, or conjugated with glucuronic acid to form ester glucuronide. The extent to which alcohols undergo the second reaction (i.e., direct conjugation with ether glucuronide) appears to depend on the rate of the first reaction; unless high doses are administered, alcohols are generally not rapidly oxidized, forming only small amounts of ether glucuronide.

Toxicity Data
LCLo (Rat) = 2,220 mg/m³/6h Interactions ...Cynanchase loses activity within 30 minutes in the presence of triethanolamine stearate, tripalmitate, and cetyl alcohol. Non-human Toxicity Values Guinea Pig Dermal LD50 < 10 g/kg Rat Oral LD50 5 g/kg Rat Intraperitoneal LD50 1600 mg/kg Mouse Oral LD50 3200 mg/kg Mouse Intraperitoneal LD50 1600 mg/kg

[1]. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216.

[2]. Anti-proliferative effect of novel primary cetyl alcohol derived sophorolipids against human cervical cancer cells HeLa. PLoS One. 2017 Apr 18;12(4):e0174241.

Hexadecane-1-ol is a long-chain primary fatty alcohol, formed by replacing the hydroxyl group at the 1-position of hexadecane. It is a human metabolite, an algal metabolite, a plant metabolite, and a flavoring agent. It is a long-chain primary fatty alcohol and also a type of hexadecyl alcohol. Cetyl alcohol, also known as 1-hexadecyl alcohol or n-hexadecyl alcohol, is a 16-carbon fatty alcohol with the chemical formula CH3(CH2)15OH. It can be prepared by the reduction reaction of palmitic acid. Cetyl alcohol is a waxy white powder or flakes at room temperature, insoluble in water but soluble in alcohols and oils. Discovered by Chevrenl in 1913, cetyl alcohol is one of the oldest known long-chain alcohols. It may be found in cosmetics and personal care products such as shampoos, creams, and lotions. Cetyl alcohol is mainly used as a sunscreen, emulsifier, and thickener, capable of altering the consistency of liquids and enhancing and stabilizing foaming ability. Due to its water-retaining properties, cetyl alcohol is often used as a moisturizer to prevent dry and chapped skin. According to federal regulations of the U.S. Food and Drug Administration (FDA), cetyl alcohol is a safe synthetic fatty acid that can be used in the synthesis of food and food ingredients, provided that its total alcohol content is not less than 98% and its linear alcohol content is not less than 94%. Cetyl alcohol is also listed as an over-the-counter drug ingredient as a skin protectant to relieve skin irritation caused by poison ivy, poison oak, sumac, and insect bites. Cetyl alcohol has been reported to have mild skin or eye irritation. 1-Hexadecyl alcohol has been found in tea (Camellia sinensis), angelica (Angelica gigas), and other organisms with relevant data. Cetyl alcohol is a synthetic solid fatty alcohol and a nonionic surfactant. Cetyl alcohol is used as an emulsifier in pharmaceutical preparations. Cetyl alcohol, also known as 1-hexadecyl alcohol and palmitol, is a solid organic compound belonging to the alcohol class. Its chemical formula is CH3(CH2)15OH. At room temperature, cetyl alcohol is a waxy white solid or flakes. It belongs to the fatty alcohol class. With the decline of commercial whaling, cetyl alcohol is no longer primarily produced from whale oil, but rather as a final product of the petroleum industry or from vegetable oils such as palm and coconut oil. Cetyl alcohol is produced from palm oil, hence one of its alternative names is palm alcohol.
See also: cetyl alcohol; cetyl palmitate; tylosap (ingredient); moringa leaf oil (partial); C14-18 alcohol (note moved to)...see more...

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Drug Indications
No drug indications. Can be used as an indirect additive to food contact substances, or as a commercial or cosmetic ingredient.

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Mechanism of Action
Cetyl alcohol has moisturizing properties, making it a suitable emulsifier and stabilizer in pharmaceutical preparations. It is also present in washable ointment bases due to its dispersibility and stability. The potential antibacterial activity of cetyl alcohol may result from altered cell membrane permeability, which hinders the absorption of essential nutrients and induces the outward diffusion of important cellular components. The proposed mechanism of action is believed to be similar to that of other long-chain fatty alcohols with the same antibacterial activity, such as myristicin and behenol.

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Therapeutic Uses
Synthetic surfactants (Exosurf) and their non-surfactant components, tylosaprol and cetyl alcohol, can act as antioxidants; in vivo infusion can reduce hyperoxia-induced injury in rats.

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Pharmacodynamics
Cetyl alcohol has a protective effect on the skin against skin irritation caused by bites, rashes, and stings. Cetyl alcohol has been reported to inhibit the growth of Mycoplasma gallisepticum and Mycoplasma pneumoniae.

C16H31D3O

245.46

245.28

75736-52-6

1-Hexadecanol;36653-82-4

2682

FLAKES FROM ETHYL ACETATE
SOLID OR LEAF-LIKE CRYSTALS
White crystals
UNCTUOUS, WHITE FLAKES, GRANULES, CUBES, OR CASTINGS
White, waxy solid

5.46

1

1

14

17

123

0

CCCCCCCCCCCCCCCCO

BXWNKGSJHAJOGX-UHFFFAOYSA-N

InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3

hexadecan-1-ol

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)