Unlock Radiant Skin and Revolutionary Healing: The Transformative Power of Retinoic Acid!

retinoic acid cas 302-79-4

Retinoic Acid, all trans is the oxidized carboxylic acid form of retinol, known in the dietary context as Vitamin A. Retinal (sc-210778) is the aldehyde form of retinol required by the retina of the eye for light absorption and visual processing.Retinoic acid and the other retinoids are involved in a broad range of biological regulations, mediating differentiation, proliferation, and apoptosis.

Binding of Retinoic Acid to the nuclear receptors RAR (retinoic acid receptor) and the RXR (retinoid X receptor) initiate signals for transcription and development.The intimate relationship between retinoids and cell cycle regulation has been implicated in suppression of oncogenic proliferation. Also available in a photoactivatable, caged form (sc-202089).

Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha.

Potent modulator of growth and differentiation. Exerts its effects by binding to nuclear retinoic acid receptors (RARs) which directly regulate gene expression. Inhibits melanocyte adhesion, motility, and growth. Has keratolytic activity.

Induces differentiation of tumor cells of neural origin. Induces apoptosis in acute promyelocytic carcinoma cells.

Properties

Retinoic acid Properties

Alternate Names:Vitamin A acid

Application:Retinoic Acid, all trans is an oxidized carboxylic acid form of Vitamin A, and an activator of RAR and RXR and used in stem cells

CAS Number:302-79-4

Purity:≥98%

Molecular Weight:300.40

Molecular Formula:C20H28O2

Supplemental Information:This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.

SAFETY

Symbol(GHS):GHS07,GHS08,GHS09

Signal word:Danger

Hazard statements:H302-H315-H360FD-H410

Precautionary statements:P202-P264-P273-P301+P312-P302+P352-P308+P313

Hazard Codes:T,Xn,N

Risk Statements：22-63-38-20/21/22-51/53

Safety Statements：53-26-36/37/39-45-36/37-61-24/25

RIDADR：3249

WGK Germany：3

RTECS:VH6475000

F:7-8-16-23

TSCA:Yes

HazardClass:6.1(b)

PackingGroup:III

HS Code:29362100

Toxicity:LD50 (10 day) in mice, rats (mg/kg): 790, 790 i.p.; 2200, 2000 orally (Kamm)

Retinoic acid Chemical Properties,Uses,Production

Dermatology drugs

Retinoic acid（Tretinoin） is commonly used in dermatology drugs, which is the department of vitamin A (Victoria methanol) metabolic intermediates.It mainly affects the growth of bones and epithelial metabolism, can promote epithelial cell proliferation and updates, and can inhibit the proliferation and differentiation of keratinocytes, so hyperkeratosis can be back to normal.

Therefore many complete or incomplete keratosis, hyperkeratosis of diseases have a certain therapeutic effect, treat a variety of skin diseases. The use of the drug can penetrate topical skin quickly, enable significantly increased epithelial cell turnover.

This class of drugs has strong and rapid inhibition on the secretion of the sebaceous glands, can reduce sebum secretion.

In addition, the product also has anti-tumor, promote wound healing and anti-inflammatory effects.

Clinical application

Retinoic acid is mainly used in the treatment of psoriasis, ichthyosis, follicular keratosis, acne, lichen planus, verrucous epidermal nevus, impetigo, vitiligo, lichen psoriasis, the face of pityriasis alba, etc.

In addition, the drugs also have some preventive effect on skin cancer.

Tretinoin Cream

Pharmacological action

Retinoic acid can induce epidermal hyperplasia, and improve the granular layer and the cell layer thickness.It can influence the silk protein process and the formation of cross-linked film and promote the differentiation of epidermal granular layer cells in the late stage of the differentiation of the epidermal cells by affecting K10, K1 keratin solution.

This product can significantly inhibit the formation of experimental acne, prevent and eliminate acne lesions.

Tretinoin also affect melanocyte cell melanogenesis , it has more than a number of functional points, having inhibitory effect on the activity of Tyrosine hydroxylase, dopa oxidase and two hydroxyindole oxidase three catalyzing enzyme, so as to reduce the formation of melanin, reduce skin pigmentation.

It has no effect on the normal black prime cellular tyrosinase activity and black pigment composition.

Pharmacodynamics

Tretinoin can increase the cell nucleus division and epidermal cell turnover, form of the stratum corneum cell adhesion, and easy to fall off.

It can remove the existing acne, while inhibiting the formation of new acne, hair follicle epithelial replacement can prevent the blockage of the plug. The synthesis of keratin is also inhibited, which can affect the metabolism of epithelial cells.

It has the effect of promoting the proliferation and differentiation of epithelial cells, and the dissolution of keratinocytes.

Pharmacokinetics

External use has a small amount of skin absorption, large area of application of the increase in absorption. About 5% of the amount of external use urine.

This product is absorbed well, the blood can reach the concentration peak after 3 hours, blood concentration can reach 0.3~0.5mg/ml, after oral administration of 1 mg/kg.

After oral absorption, it is widely combination with plasma protein and has half-life of 0.7 h in a mean elimination. After a single oral dose of 40mg, blood drug concentration can be up to the source metabolic level in 7~12 hours.

Multiple oral administration has not seen in vivo accumulation, but the blood concentration of the drug is significantly decreased, which may be due to the induction of cytochrome P450 enzymes, and the elimination of the rate of increase and bioavailability.

It mainly used in the liver metabolism, which is metabolites of glucose acid esters. 60% of metabolites is by renal excretion, and can also be excreted by bile but metabolite half-life is longer.

Vitamin A acid medicine

Vitamin A acid medicine is a kind of natural or synthetic existence with vitamin A activity of retinol (retinol) derivatives. The drug discovery is regarded as a new milepost for treatment of skin diseases and cosmetic pharmacology.

In the last 20 years, the application of the dimension A acid has made great progress in the treatment of many skin diseases. So far, there have been 2500 retinoic acid derivatives.

According to its development process and chemical structure, they can be divided into three generations: the first generation is class of non aromatic retinoid, tretinoin and isotretinoin as the representative.

The second generation is class of single aromatic A acids, etretinate and acitretin as the representative; the third generation is class of aromatic dimensional A acid, aromatic methyl ethyl acetylene, adapalene and vitamin A acid ethyl ester as the represented.

 

use of of vitamin A in skin diseases

The indications

Used in the treatment of acne vulgaris, especially the blackhead acne lesions, senile, fluorescent or drug skin atrophy, ichthyosis and various abnormal keratinization and pigment excessive calm skin disease, and psoriasis.

Drug interaction

(1)Retinoic acid combining with light sensitive drugs can increase the risk of photosensitiveness.

(2)Retinoic acid combining with soap and detergents, containing keratolytic agents (such as peroxy benzoic acid, Resorcinol, salicylic acid, sulfur,etc), ethanol preparation, isotretinoin can aggravate irritation or dryness to skin, and therefore must be used with caution.

(3) Retinoic acid combining with sago cimetidine, cyclosporine and diltiazem, verapamil and ketoconazole, can cause an increase in the blood concentration of the drug, and may lead to retinoic acid poisoning.

(4 Retinoic acid combining with pentobarbital, rifampicin, phenobarbital, can cause the blood concentration of the product decreasing.

(5) The product will affect the liver cytochrome P450 enzyme system, resulting in changes in blood concentrations of the drug.

(6)Taking drugs oryzanol, vitamin B1, vitamin B6 with Tretinoin, can make headache relieved or disappeared, because of adverse reactions of the drug.

Uses

(1) Applies to abnormal tyshiyongyupe of acne, fish phosphorus disease and abnormal psoriasis.

(2) Resistance to abnormal skin drugs.

(3) Tretinoin mainly affects the growth of bones and epithelial metabolism, can promote epithelial cell proliferation and updates, and can inhibit the proliferation and differentiation of keratinocytes, so hyperkeratosis can be back to normal.

Therefore many complete or incomplete keratosis, hyperkeratosis of diseases have a certain therapeutic effect, treat a variety of skin diseases.

Tretinoin is mainly used in the treatment of psoriasis, ichthyosis, follicular keratosis, acne, lichen planus, verrucous epidermal nevus, impetigo, vitiligo, lichen psoriasis, the face of pityriasis alba, etc.

Indications and Usage

Retinoic acid is a commonly used dermatological drug and an intermediate product in bodily vitamin A (dimethyl alcohol) metabolism. It has a similar odor to that of vitamin A acetate.

It is easily soluble in methanol, ethanol, acetone, chloroform, dichloromethane, and it is also soluble in vegetable oil and fats. It is instable when in contact with light and heat, hygroscopic in air, and polymerizes and metamorphosizes when in contact with water.

Retinoic acid also anti-tumor, wound-healing, and infection-resisting effects.

It is mainly used clinically to treat psoriasis, hair follicle keratosis, acne, lichen planus, verrucous epidermis nevus, ureophora, vitiligo, pityriasis rosea, and facial pityriasis simplex, especially blackhead skin lesions, and senile, sun-induced, or drug induced skin atrophy, as well as various keratosis abnormalities and hyperpigmentation diseases.

In addition, it also has certain preventative effects against skin cancer. Retinoic acid can significantly inhibit experimental acne breakouts.

Mechanisms of Action

Retinoic acid mainly affects bone growth and epithelium metabolism, it can promote epithelium cell growth and renewal, and it can inhibit keratinocyte growth and differentiation to correct hyperkeratosis.

Thus, it has certain curative effects on diseases related to keratinization, hypokeratinization and hyperkeratinization. A localized application can penetrate the skin very quickly and cause significant growth in epithelial cells.

Retinoic acid has a strong and rapid inhibiting effect on sebaceous glands and can reduce sebum secretion.

Retinoic acid promotes epidermal growth, thickens the stratum granulosum and stratum spinosum, and affects K1 and K10 keratinysis in late stage epidermal cell differentiation to influence the siloxin to silymeric protein process and cross-linked coating formation, thus promoting epidermal granulosa cells to differentiate towards the cuticle layer.

It regulates follicular sebaceous gland epithelium keratinization abnormalities to remove keratin plugs, thus being able to prevent and remove acne lesions, and follicular epithelial renewal can also prevent keratin plugs and acne formation.

In addition, retinoic acid can also affect melanogenesis of melanocytes with a multi-site effect, and it can inhibit the activity of tyrosine hydroxylase, dopa oxidase, dihydroxyl indole oxidase, and other type-three catalytic enzymes, thus lowering the formation of melanin and reducing hyperpigmentation.

It has not impact on normal human melanocyte tyrosinase activity and melanin content.

Chemical Properties

Yellow-Orange Powder

Uses

retinoic acid (tretinoin) is a vitamin A derivative. It has demonstrated an ability to alter collagen synthesis, increase dermal hyaluronic acid levels, and stimulate fibroblast growth and the extracellular matrix. It is used for keratinization disorders and for treating acne.

Retinoic acid’s anti-aging effect has been convincingly documented and it is often used for treating the visible signs of aging, though these results can take approximately 6 months to be visible.

It is associated with a number of adverse effects, including irritation, photosensitivity, skin dryness, redness, and peeling. It should also not be used while pregnant.

Uses

Physiological metabolite of vitamin A. Effects gene expression via nuclear retinoic acid receptors (RAR); mediates cellular growth and differentiation

Definition

ChEBI: Retinoic acid is a retinoid in which all four exocyclic double bonds have E- (trans-) geometry. It is a naturally occurring derivative of vitamin A (retinol).

Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis.

Indications

Topical tretinoin (Retin-A, Renova, Avita), like isotretinoin, alters keratinization in the acroinfundibulum. In addition, it reverses certain premalignant and other histological changes associated with the photoaging changes that accompany chronic exposure to ultraviolet radiation.

Topically applied tretinoin is indicated in comedogenic and papulopustular acne vulgaris, and its mild exfoliative effects make it sometimes useful in molluscum contagiosum, flat warts, and some ichthyotic disorders. It is often prescribed to lessen the clinical signs of photoaging (wrinkling and hyperpigmented macules).

Manufacturing Process

100 parts of beta-ionol are dissolved in 200 parts of dimethylforrnamide and after the addition of 165 parts of triphenylphosphine hydrobromide, stirred for 7 hours at room temperature.

Then 70 parts of 4-methyl-1-al-hexadiene- (2,4)-acid-(6) (melting point 177°C, white needles from water) are added to the now clear solution. 150 parts of isopropanol are added and the whole cooled to -30°C.

Into this solution, while stirring vigorously, 190 parts by volume of a 30% solution of sodium methylate in methanol are allowed to flow in. A vigorous exothermic reaction takes place and the temperature in the interior of the flask rises to +5°C.

It is stirred for another 5 minutes and neutralized with 10% of sulfuric acid (until acid to Congo).

After stirring for 2 hours at room temperature, the mass of vitamin A acid has crystallized out. It is sharply filtered off by suction and washed with a little ice-cold isopropanol.

From the filtrate, a further small amount of mainly all trans vitamin A acid crystallizes out upon the addition of water. The filter cake is suspended in 600 parts of water and stirred for 4 hours at room temperature; it is filtered by suction and the product washed with water.

It is dried in vacuo at 40° to 50°C and 115 parts of vitamin A acid are obtained. The melting point lies between 146° and 159°C.

The mixture of the all trans and mainly 9,10-cis vitamin A acid may be separated by fractional crystallization from ethanol.

All trans vitamin A acid has a melting point of 180° to 182°C and 9,10-cis vitamin A acid, which crystallized in the form of pale yellow fine needles collected into clusters, has a melting point of 189° to 190°C.