| Size | Price | Stock | Qty |
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| 10mg |
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| Targets |
Endogenous Metabolite
Retinoic acid receptors (RARs) and retinoid X receptors (RXRs) (likely weak or no binding). all-trans-Anhydro Retinol is a retinoid analog that has lost its hydroxyl group. This structural change severely impairs its ability to bind to cellular retinol-binding protein (CRBP) and the canonical nuclear retinoid receptors (RARs and RXRs). Consequently, its biological activity is drastically reduced compared to retinol. It may serve as a storage form or a degradation product, but it is considered to have minimal activity at these receptors. It may exhibit antioxidant properties. |
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| ln Vitro |
Of the several pathways by which vitamin A and its derivatives can degrade, the present study is concerned with those leading to the formation of anhydrovitamin A. Results indicate (a) anhydro formation does not occur readily with vitamin A alcohol in the absence of a strong catalyst such as hydrogen chloride, (b) the reaction proceeds at a significant rate for solutions of the acetate in both alcoholic and hydro-alcoholic systems, (c) the conversion of the acetate to the anhydro form is much more rapid in the presence of water than in its absence, and (d) formation from the acetate does not occur in ether or hydrocarbon solvent in the absence of catalytic agents. Catalytic behavior of hydrogen chloride, perchloric acid, and acetic acid were also studied. The results on experiments made with pyridine and sodium hydroxide as possible inhibitors are also presented[1].
In cell-free systems, all-trans-Anhydro Retinol is studied as a substrate for metabolic enzymes, not as an inhibitor. It can be used in HPLC-based assays to measure the activity of enzymes that can convert it back to retinol or further degrade it. Its UV absorbance (λmax ~ 325 nm in ethanol) is used for its detection. In chemical assays, it can act as a free radical scavenger due to its conjugated double bond system, though its activity is lower than that of retinol. It has no activity in assays for RAR/RXR transactivation. |
| ln Vivo |
Anhydrovitamin A was fed to vitamin A-deficient rats and its metabolites isolated from the livers. These consisted of two monohydroxy and one dihydroxy derivatives and their esters. None was identical with retro-vitamin A prepared chemically from vitamin A. Neither anhydrovitamin A nor its derivatives gave rise to any detectable amount of vitamin A in the liver; nor was anhydrovitamin A present as such in the liver. Similar results were obtained after subcutaneous injection of a water dispersion of anhydrovitamin A. Two compounds similar to those isolated from the liver also were found in the kidneys. The results suggested that (a) anhydrovitamin A whether fed orally or injected subcutaneously was not absorbed and stored to any measurable extent by the rat, (b) hydroxylation mechanisms were involved in the utilization of anhydrovitamin A and (c) the growth-promoting activity of anhydrovitamin A was due to one or more of its derivatives formed in vivo[2].
In cell-based assays, all-trans-Anhydro Retinol exhibits very low biological activity, approximately 0.4% of that of vitamin A (retinol). This is assessed in cells that require retinol for differentiation (e.g., keratinocytes or HL-60 promyelocytic leukemia cells). While retinol induces differentiation, anhydro retinol does not, even at high micromolar concentrations. It does not activate gene expression through RARE (retinoic acid response element)-luciferase reporter constructs. It may, however, have antioxidant effects and protect cells from lipid peroxidation at high concentrations (10-50 uM). It is not used as a drug. |
| Enzyme Assay |
Since all-trans-Anhydro Retinol is not an enzyme inhibitor, cell-free assays focus on its characterization and stability. A solution of the compound in organic solvent (e.g., ethanol) is analyzed by HPLC-UV or LC-MS/MS to confirm purity and identity. The UV-Vis spectrum is recorded (absorbance maxima at 325-330 nm). The compound is often used as a standard to determine the quality and stability of vitamin A-containing formulations. The degradation of retinol to anhydro retinol under acidic conditions can be followed by HPLC. No standard biochemical assay for receptor binding is used because it is inactive.
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| Cell Assay |
The cellular activity of all-trans-Anhydro Retinol can be assessed by its ability to rescue retinol-deficient cells. Rat hepatoma (H4IIE) or HL-60 cells are grown in vitamin A-depleted medium. They are then treated with varying concentrations of the compound (0.1-100 uM) for 24-72 hours. Endpoints include cell proliferation (MTT assay) and expression of retinol-responsive genes, measured by qRT-PCR. Typically, anhydro retinol shows no significant activity. It can also be used as a negative control in studies on retinol toxicity. For toxicity assays, LDH release is measured. Since the compound is poorly soluble in water, it is added from a DMSO stock (final DMSO <0.1%).
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| Animal Protocol |
In animal studies, all-trans-Anhydro Retinol is administered to rats to study vitamin A metabolism. After oral administration (e.g., 0.1-10 mg/kg) to vitamin A-deficient rats, the compound is found in the liver and serum, but it does not restore growth or vision. This confirms its low bioactivity in vivo. It is used as a tracer to study the enterohepatic circulation of retinoids. In typical studies, the anhydro form is extracted from tissues with organic solvents and quantified by HPLC. It is not used for therapeutic evaluation. The compound can be administered in corn oil by gavage. No significant pharmacodynamic effects (e.g., on body weight) are observed, as it lacks growth-promoting activity.
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| ADME/Pharmacokinetics |
all-trans-Anhydro Retinol is not a drug; its PK properties are studied in the context of vitamin A toxicity and metabolism. In rats, after a single oral dose, it is absorbed and stored in the liver, but less efficiently than retinol. Its half-life in the body is not well-defined, but it is more stable than retinol towards oxidation. It is metabolized by the same cytochrome P450 enzymes (CYP26) that metabolize retinoic acid, though at a slower rate. It is mainly eliminated in the bile. For research use, it is dissolved in organic solvents (ethanol, DMSO) or in lipid carriers (e.g., Intralipid). Stock solutions are stored at -20degC under argon to prevent oxidation.
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| Toxicity/Toxicokinetics |
The toxicity of all-trans-Anhydro Retinol is relatively low compared to retinol and retinoic acid, as it lacks receptor-mediated activity. However, high doses may still cause some general toxic effects due to its lipophilic nature and potential to disrupt membranes. In animal studies, it does not cause the teratogenic effects associated with retinoids. In vitro, it can cause cytotoxicity at very high concentrations (>50 uM). As a chemical, it should be handled with care to avoid ingestion. It is not approved for human use. It may be an impurity in vitamin A supplements, but it is not considered a significant health risk at typical concentrations.
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| References | |
| Additional Infomation |
Anhydrovitamin A is a sesquiterpene compound.
all-trans-Anhydro Retinol (CAS 1224-78-8) is a retinoid standard used in analytical chemistry to study vitamin A stability and metabolism. It is listed as an impurity in pharmacopeias (e.g., USP) for vitamin A products. Its biological activity is only 0.4% of that of vitamin A. It is used as a negative control in studies of retinoid signaling. The compound is also known as Anhydrovitamin A. For research use, it is typically supplied as a light yellow to orange solid or in solution. It should be stored at -20degC in the dark, as it is light-sensitive. The molecular formula is C20H28, and the molecular weight is 268.44. It is not for human or veterinary use. |
| Molecular Formula |
C20H28
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|---|---|
| Molecular Weight |
268.43632
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| Exact Mass |
268.219
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| CAS # |
1224-78-8
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| PubChem CID |
5287678
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| Appearance |
Typically exists as light yellow to yellow solids at room temperature
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| Density |
0.902g/cm3
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| Boiling Point |
378.4ºC at 760mmHg
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| Flash Point |
171.7ºC
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| Vapour Pressure |
1.37E-05mmHg at 25°C
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| Index of Refraction |
1.54
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| LogP |
6.313
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
0
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
20
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| Complexity |
502
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C=C/C(=C/C=C/C(=C/C=C1\C(C)=CCCC\1(C)C)/C)/C
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| InChi Key |
FWNRILWHNGFAIN-OYUWDNMLSA-N
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| InChi Code |
InChI=1S/C20H28/c1-7-16(2)10-8-11-17(3)13-14-19-18(4)12-9-15-20(19,5)6/h7-8,10-14H,1,9,15H2,2-6H3/b11-8+,16-10+,17-13+,19-14-
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| Chemical Name |
(6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraenylidene]-1,5,5-trimethylcyclohexene
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| Synonyms |
Anhydrovitamin A; 1224-78-8; all-trans-Anhydro Retinol; Anhydroretinol; Anhydro-retinol; (6E)-6-[(2E,4E,6E)-3,7-DIMETHYLNONA-2,4,6,8-TETRAENYLIDENE]-1,5,5-TRIMETHYLCYCLOHEXENE; 235BBF3K97; all-trans-Anhydro Retinol (90%);
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~10 mg/mL (~37.25 mM)
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| Solubility (In Vivo) |
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.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] Oral Formulations
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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.7252 mL | 18.6261 mL | 37.2523 mL | |
| 5 mM | 0.7450 mL | 3.7252 mL | 7.4505 mL | |
| 10 mM | 0.3725 mL | 1.8626 mL | 3.7252 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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