• Isotretinoin

Isotretinoin

  • CasNo：4759-48-2
  • Purity：99%

Product Details;

CasNo： 4759-48-2

Molecular Formula： C20H28O2

Appearance： yellowish crystalline powder

Factory Supply High Grade Isotretinoin 4759-48-2 with reasonable price

  • Molecular Formula:C20H28O2
  • Molecular Weight:300.441
  • Appearance/Colour:yellowish crystalline powder 
  • Vapor Pressure:7.55E-10mmHg at 25°C 
  • Melting Point:172-175 °C(lit.) 
  • Refractive Index:1.4800 (estimate) 
  • Boiling Point:462.8 °C at 760 mmHg 
  • PKA:4.76±0.33(Predicted) 
  • Flash Point:350.6 °C 
  • PSA：37.30000 
  • Density:1.011 g/cm3 
  • LogP:5.60260 

Isotretinoin (Cas 4759-48-2) Usage

Isotretinoin is classified as a vitamin A derivative, and it exhibits a rapid and potent ability to inhibit the proliferation and differentiation of skin gland cells. This drug is particularly effective in treating severe nodular cystic acne. Isotretinoin boasts high gastrointestinal absorption but is not suitable for topical application. Its primary purpose is to address cases of severe acne that do not respond to other medications. Additionally, it shows efficacy in treating cystic acne, various types of acne, rosacea, ichthyosis, follicular keratosis, pityriasis red hair, and other dermatological conditions.

Isotretinoin falls under the category of first-generation vitamin A acids, serving as a stereoisomer of all-trans vitamin A acid. When administered orally, it exerts a pronounced anti-sebum effect, particularly beneficial for severe acne. This mechanism operates through several pathways:

  1. It reduces sebaceous gland size and inhibits their activity, thus diminishing sebum secretion and inhibiting the growth of Propionibacterium, which thrives in a lipid-rich environment.
  2. It possesses anti-keratosis properties, inhibiting excess epidermal cell proliferation and promoting differentiation. It also reduces hair follicle keratosis and sebaceous gland blockages.
  3. It impacts lymphocyte and monocyte function, curbing neutrophil chemotaxis and exhibiting anti-inflammatory effects.
  4. It selectively binds to vitamin A acid nuclear receptors, inhibiting acne rod bacilli proliferation. At low doses, it stimulates immunity, but at high doses, it suppresses immunity.
  5. It inhibits collagenase and gelatinase production in the skin, along with the activity of ornithine decarboxylase. This inhibition of ornithine decarboxylase is crucial in preventing skin mutations, contributing to isotretinoin's ability to suppress tumorigenesis.
  6. Topical application mimics the action of vitamin A acid, inducing epidermal cell proliferation, promoting granular cell layer differentiation into the stratum corneum, and regulating abnormal cornification processes in hair follicle sebaceous epithelium, ultimately serving a therapeutic role.

 

InChI:InChI=1/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/p-1/b9-6+,12-11+,15-8+,16-14-

4759-48-2 Relevant articles

Uses and complications of isotretinoin therapy

Charles N. Ellis MD, Kent J. Krach MD

, Journal of the American Academy of Dermatology Volume 45, Issue 5, November 2001, Pages S150-S157

Isotretinoin, also known as 13-cis-retinoic acid, has found its place as a valuable retinoid for the treatment of numerous dermatologic conditions, often achieving remarkable outcomes. Despite its effectiveness in various skin disorders, it's essential to note that oral retinoids come with potential side effects and toxicities, necessitating vigilant oversight by experienced medical professionals. The utilization of oral retinoids in clinical practice continues to broaden, extending beyond the realm of dermatology, reflecting their growing significance in medicine.

Preventing and Managing the Side Effects of Isotretinoin

Brelsford, Megan 1 ; Beute, Trisha Clarke 2 ;

, 1 September 2008, vol. 27, no. 3, pp. 197-206(10)

Isotretinoin, also known as 13-cis-retinoic acid, is extensively utilized for treating severe acne, disorders related to skin conification, psoriasis, and skin cancer prevention. As a member of the retinoid family, it encompasses a broad range of potential side effects, spanning reproductive, cutaneous, ocular, neurological, musculoskeletal, and hepatic issues. When patients can withstand these side effects, it emerges as a highly effective treatment option. This article delves into both the most prevalent and the most concerning side effects, while also exploring strategies for healthcare providers and patients to effectively manage them, thus enabling the beneficial use of isotretinoin treatment.

4759-48-2 Process route

[(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

[(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

trans-β-formyl crotonic acid
54168-84-2

trans-β-formyl crotonic acid

9-cis-retinoic acid
302-79-4,3555-80-4,4759-48-2,5300-03-8,5352-74-9,68070-34-8,68070-35-9,97950-17-9,98462-64-7,124510-04-9

9-cis-retinoic acid

Conditions
Conditions Yield
[(2Z,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride; trans-β-formyl crotonic acid; With sodium hydroxide; In isopropyl alcohol; at -50 - -40 ℃; for 24h; Inert atmosphere;
With hydrogenchloride; palladium diacetate; In isopropyl alcohol; at 80 ℃; pH=8-9; Inert atmosphere;
82.3%
ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
86708-67-0,24519-09-3

ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

9-cis-retinoic acid
302-79-4,3555-80-4,4759-48-2,5300-03-8,5352-74-9,68070-34-8,68070-35-9,97950-17-9,98462-64-7,124510-04-9

9-cis-retinoic acid

Conditions
Conditions Yield
With potassium hydroxide; In ethanol;
100%
With potassium hydroxide; In ethanol; at 50 ℃;
98%
With potassium hydroxide; In ethanol; water; at 70 ℃;
91%
With potassium hydroxide; In ethanol; at 70 ℃;
91%
With sodium hydroxide; In methanol; at 50 ℃; for 0.5h;
74%
With sodium hydroxide; In methanol; at 50 ℃;
70%
With sodium hydroxide; In ethanol; Yield given; Heating;
 

4759-48-2 Upstream products

  • 638-10-8
    638-10-8

    ethyl 3-methylbut-2-enoate

  • 3917-41-7
    3917-41-7

    (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

  • 81176-73-0
    81176-73-0

    11-cis,13-cis-12-carboxyretinoic acid

  • 3899-20-5
    3899-20-5

    ethyl retinoate

4759-48-2 Downstream products

  • 16760-45-5
    16760-45-5

    (2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

  • 84680-31-9
    84680-31-9

    13-cis-N-(4-Hydroxybutyl)retinamide

  • 138752-02-0
    138752-02-0

    all-(E)-retinoic and 13-(Z)-retinoic anhydride

  • 73174-99-9
    73174-99-9

    13-cis-retinoyl chloride

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