In 7 men with mild hypercholesterolemia, dietary supplementation with Docosanoic acid (behenic acid, 22:0) via behenate oil resulted in mean total cholesterol (5.87 ± 0.8 mmol/L) and LDL cholesterol (4.40 ± 0.8 mmol/L) concentrations not significantly different from those of palm oil (rich in palmitic acid: total cholesterol 5.84 ± 0.7 mmol/L, LDL cholesterol 4.42 ± 0.7 mmol/L) [1]
The total cholesterol and LDL cholesterol concentrations induced by docosanoic acid were significantly higher than those of high–oleic acid sunflower oil (total cholesterol 5.12 ± 0.5 mmol/L, LDL cholesterol 3.70 ± 0.6 mmol/L) [1]
No significant differences in triacylglycerol or HDL cholesterol concentrations were observed among the three diet groups (behenate oil, palm oil, high–oleic acid sunflower oil) [1]
Plasma triacylglycerol fatty acid analysis showed only a small amount of docosanoic acid (1.0 ± 1.0% by wt) in the behenate oil group; the total saturated fatty acid content (30.4 ± 3.3% by wt) was significantly higher than that of high–oleic acid sunflower oil (24.8 ± 2.5% by wt) but not different from that of palm oil (33.1 ± 2.3% by wt) [1]

Human metabolic ward study (randomized, single-blind, crossover design): Seven men aged 55–75 y (BMI 27 ± 5) with mild hypercholesterolemia (baseline total cholesterol 5.69 ± 0.54 mmol/L) were recruited. The study included 3 diet periods (each 3 wk), separated by ≥1 wk of ad libitum outpatient diet. Each diet consisted of low-fat natural foods plus one fat supplement (behenate oil, palm oil, or high–oleic acid sunflower oil). The overall diet energy composition was 53% fat, 35% carbohydrate, and 12%. The base diet provided 10% of total fat (3% saturated, 4% monounsaturated, 3% polyunsaturated) and 91 mg/d dietary cholesterol. Fat supplements provided 43% of daily energy; behenate oil contained 39.5% docosanoic acid, and its daily allotment was increased by 24% to ensure equal absorbable energy from test fats. Patients consumed all foods under supervision, with daily interviews to confirm intake. Body weight was maintained constant by adjusting total energy intake. During the final 4 d of each diet period, blood was drawn after a 14-h fast for lipid, lipoprotein, and plasma fatty acid analysis [1]

Absorption: The absorption rate of docosanoic acid in the human body is about 30%, which is much lower than that of palmitic acid (95-98%) [1] Metabolism: After absorption, docosanoic acid can be hydrolyzed into short-chain saturated fatty acids (such as myristic acid, palmitic acid, stearic acid) [1] Distribution: Only a small amount of intact docosanoic acid is distributed in the plasma triglyceride pool [1] Excretion: No specific parameters of docosanoic acid excretion have been reported [1]

Toxicity Summary
The oral LD50 of docosanoic acid in rats is greater than 2000 mg/kg. No data on irritation or sensitization are currently available. In an oral study using the OECD combined repeated-dose and reproductive/developmental toxicity study [OECD TG 422], rats were administered docosanoic acid for at least 42 consecutive days at doses of 0, 100, 300, and 1000 mg/kg/day. No deaths were observed, and no toxic effects related to the substance were observed in any parameter. Therefore, the no-observed-adverse-effects-alteration-effects (NOAEL) for docosanoic acid is considered to be 1000 mg/kg/day, including repeated-dose toxicity and reproductive/developmental toxicity. The chemical was negative in bacterial mutagenicity assays [OECD TG 471, 472] and in vitro chromosomal aberration assays [OECD TG 473]. …The acute toxicity values of docosanoic acid to algae (Selenastrum capricornutum), aquatic invertebrates (Daphnia magna), or fish (Oryzias latipes) are greater than those at its water solubility (0.016 mg/L). In a 21-day breeding study on Daphnia magna, its no-effect concentration (NOECD) was also greater than its water solubility. No significant effects were observed in any extremely high concentration studies using dispersants under OECD testing guidelines [TG201, 202, 203, 204, or 211]. Information suggests that some shorter-chain fatty acids do not cause mortality in certain aquatic organisms (freshwater amphipods; marine killifish) at saturation concentrations. Considering these and other information, it is reasonable to assume that docosanoic acid is non-toxic to aquatic organisms at concentrations below its water solubility (0.016 mg/L). Since the obtained no-effect concentration (NOEC) value was higher than the water solubility of the substance, the predicted no-effect concentration (PNEC) was not calculated.

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Interaction
Addition of calcium ions enhanced the platelet aggregation effect of behenic acid on washed porcine platelets. When added at equimolar concentrations, linoleic acid completely inhibited the effect of behenic acid.

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Non-human toxicity values
Oral LD50 in rats >2,000 mg/kg / Purity 85.9%; Impurities: (C14-C20) fatty acids 10.9%, C24 fatty acids 2.3%/

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Subjects tolerated the diet rich in docosanoic acid well and did not experience significant gastrointestinal discomfort or adverse reactions associated with high testosterone oil intake [1]

[1]. Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4.

Docosanoic acid (DoCSA) is a straight-chain, C22-carbon long-chain saturated fatty acid that plays a role in plant metabolism. It is both a straight-chain saturated fatty acid and a long-chain fatty acid, and is also the conjugate acid of behenic acid. DoCSA has been reported in Calodendrum capense, Arisaema tortuosum, and other organisms with relevant data. Behenic acid is a saturated, very long-chain fatty acid with a 22-carbon backbone. Behenic acid is the main component of Moringa seed oil. See also: Borage seed oil (partial).

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Behenic acid (22:0) is a long-chain saturated fatty acid[1]
Due to its long chain length, the human body has a very low absorption rate of it (≈30%)[1]
Its cholesterol-raising potential is comparable to that of palmitic acid, and therefore it is not suitable as a substitute for palmitic acid in synthetic triglycerides[1]
Its cholesterol-raising mechanism may involve degradation into short-chain saturated fatty acids known to raise cholesterol[1]

C22H44O2

340.5836

340.334

112-85-6

16529-65-0 (zinc salt);18990-72-2 (aluminum salt);20259-31-8 (iron(+3) salt);2489-05-6 (silver(+1) salt);2636-16-0 (barium salt);34303-23-6 (cadmium salt);4499-91-6 (lithium salt);5331-77-1 (hydrochloride salt);7211-53-2 (potassium salt)

8215

Off-white to light yellow solid powder

0.9±0.1 g/cm3

391.8±5.0 °C at 760 mmHg

72-80 °C(lit.)

176.3±12.5 °C

0.0±0.9 mmHg at 25°C

1.459

10.34

1

2

20

24

250

0

UKMSUNONTOPOIO-UHFFFAOYSA-N

InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)

docosanoic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.

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

DMSO : ~1.43 mg/mL (~4.20 mM)
H2O : ~1 mg/mL (~2.94 mM)

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.)