Absorption, Distribution and Excretion
This report describes a novel human disease characterized by the accumulation of long-chain n-alkanes from plants in the internal organs. Lipid analysis of tissues from a suddenly deceased adult male with diffuse visceral granuloma containing lipophilic crystalline material revealed the presence of anomalous compounds identified as long-chain n-alkanes containing 29 carbon atoms (n-nonacosane), 31 carbon atoms (n-hexadecane), and 33 carbon atoms (n-trisane). The distribution of n-alkanes in the patient's tissues showed that these compounds primarily accumulated in the lumbar aortic lymph nodes, adrenal glands, lungs (highest concentration in pulmonary granulomas), and liver; significantly lower concentrations were detected in the myocardium and kidneys, and none were detected in brain tissue. Based on the structural composition and tissue distribution of the accumulated n-alkanes, this article explores their dietary (plant) sources and the pathophysiological mechanisms of storage. Arthrobacter nana KCC B35, isolated from densely covered cyanobacterial mats on oil deposits along the Arabian Gulf coast, exhibits excellent growth using C10 to C40 n-alkanes as its sole carbon and energy source. Its growth on C20 to C40 alkanes is even superior to that on C10 to C18 alkanes. After co-culturing biomass samples with n-octacosane (C28) or n-nonacosane (C29) for 6 hours, these compounds became the major constituent alkanes of the cellular hydrocarbon composition. Even-chain hexadecane (C16) and odd-chain pentadecane (C15) were the second-largest constituent alkanes in C28 and C29 cultured cells, respectively. Compared to control cells not incubated with hydrocarbon compounds, cells incubated with n-hexadecane accumulated a higher proportion of C16 fatty acids in their lipids. On the other hand, no fatty acids of the same chain length were detected in cells incubated with C28 and C29, but the fatty acid profiles of the cellular lipids suggest that these ultra-long-chain alkanes may have undergone medium-chain oxidation. This activity makes the tobacco nitrogen-fixing bacterium KCC B35 suitable for use in mixed formulations for the bioremediation of environments contaminated by heavy oil deposits.

Toxicity Summary
Identification and Uses: Nonacosane is a higher n-alkane containing 29 carbon atoms (C29). Human Exposure and Toxicity: A case report describes a human illness characterized by the accumulation of long-chain n-alkanes from plants in the viscera of patients. Diffuse visceral granulomas contained lipophilic crystalline substances, indicating the presence of long-chain n-alkanes, including nonacosane. Studies of the distribution of n-alkanes in patient tissues showed significant accumulation in the lumbar aortic lymph nodes, adrenal glands, lungs, and liver; significantly lower levels were detected in the myocardium and kidneys, while no levels were detected in brain tissue. Animal Studies: Nonacosane can cause "paraffin liver" in cattle. The abnormal substance was found in very high levels in the bovine liver, indicating low toxicity and clearly due to long-term accumulation.

[1]. A New 3-Prenyl-2-flavene and Other Extractives from Baphia massaiensis and Their Antimicrobial Activities. Natural Product Communications.

Nonacosane is a straight-chain alkane consisting of 29 carbon atoms. It is a plant metabolite and a component of volatile oils. It has been reported to exist in Vanilla madagascariensis, Echinacea angustifolia, and other organisms with relevant data. See also: Moringa leaf oil (partial).

C29H60

408.7867

408.47

630-03-5

12409

White to off-white solid

0.805g/cm3

286 °C15 mm Hg(lit.)

63-66 °C(lit.)

291.2ºC

1.45

11.558

0

0

26

29

231

0

C([H])([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

IGGUPRCHHJZPBS-UHFFFAOYSA-N

InChI=1S/C29H60/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-29H2,1-2H3

nonacosane

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)

DMF :< 1 mg/mL

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.)