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레티노산

레티노산
레티노산 구조식 이미지
카스 번호:
302-79-4
한글명:
레티노산
동의어(한글):
레티노산;RE주석산;레틴산;레티노익애씨드;트라이테노인;트라이테노인(레티노익애씨드및그염류)
상품명:
Retinoic acid
동의어(영문):
ATRA;aberel;eudyna;Atragen;retin-a;tretinm;aknoten;beta-ra;Aberela;gn100335
CBNumber:
CB3222630
분자식:
C20H28O2
포뮬러 무게:
300.44
MOL 파일:
302-79-4.mol

레티노산 속성

녹는점
180-181 °C (lit.)
끓는 점
381.66°C (rough estimate)
밀도
1.0597 (rough estimate)
굴절률
1.4800 (estimate)
저장 조건
-20°C
용해도
Practically insoluble in water, soluble in methylene chloride, slightly soluble in ethanol (96 per cent).
산도 계수 (pKa)
4.73±0.33(Predicted)
물리적 상태
powder
색상
yellow
수용성
insoluble
감도
Light Sensitive
Merck
14,8165
BRN
2057223
안정성
Store Dry in Freezer at -20°C for up to 1 year; in Solution at -20°C for up to 3 Months.
InChIKey
SHGAZHPCJJPHSC-ZVCIMWCZSA-N
CAS 데이터베이스
302-79-4(CAS DataBase Reference)
EPA
Retinoic acid (302-79-4)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T,Xn,N
위험 카페고리 넘버 22-63-38-20/21/22-51/53
안전지침서 53-26-36/37/39-45-36/37-61-24/25
유엔번호(UN No.) 3249
WGK 독일 3
RTECS 번호 VH6475000
F 고인화성물질 7-8-16-23
TSCA Yes
위험 등급 6.1(b)
포장분류 III
HS 번호 29362100
유해 물질 데이터 302-79-4(Hazardous Substances Data)
독성 LD50 (10 day) in mice, rats (mg/kg): 790, 790 i.p.; 2200, 2000 orally (Kamm)
기존화학 물질 KE-11883
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H361 태아 또는 생식능력에 손상을 일으킬 것으로 의심됨 생식독성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P405 밀봉하여 저장하시오.

레티노산 MSDS


3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid

레티노산 C화학적 특성, 용도, 생산

화학적 성질

Yellow-Orange Powder

Originator

Aberel,McNeil,US,1973

용도

keratolytic, antiacne, antineoplastic

용도

antipruritic

용도

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

용도

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.

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).

정의

ChEBI: A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.

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.

상표명

A-acido;Acid a vit;Acnavit;Acnavyse;Acretin;Airoderm;Aknebon;Aknefug;Anition;Antibio-aberel;Apsor;A-vitamisyre;Avitoin;Cordes vas;Dermoclar;Dermojuventas;Derugin;Locacid;Pigmanorm;R0 22-6595;Reiderma;Retin a;Ro 1-5488;Sebo-psor;Stie vaa;Stievaa;Tretin m;Vas dexa;Verra-med;Vitacid a.

Therapeutic Function

Keratolytic

World Health Organization (WHO)

Tretinoin, a retinol derivative, was introduced in 1973 exclusively for the topical treatment of severe acne. Preparations of tretinoin are indicated for topical use only since oral administration has been associated with risk of toxicity from hypervitaminosis-A and subsequently of teratogenicity.

일반 설명

Tretinoin is available in 10-mg capsules for oral administrationin the treatment of APL. The mechanism of action involvespassive diffusion through the cell membrane andthen movement to the nucleus where it interacts with theretinoic acid receptor (RAR) portion of the PML-RAR fusionprotein. Binding of tretinoin allows the cell to differentiateand has also been shown to result in the destruction ofthe PML-RAR fusion protein. Resistance to tretinoin isproblematic and associated with an increase in cellularretinoic acid–binding proteins (CRAPBs) located in the cytosol.The complexation with tretinoin prevents movementinto the nucleus and may present the drug to metabolizingenzymes that inactivate it. Amino acid mutation of thePML-RAR protein has also been established as a mechanismof resistance. The agent is well absorbed upon oral administrationand highly (95%) protein bound. Metabolismoccurs in the liver and several inactive metabolites havebeen identified including 13-cis-retinoic acid, 4-oxo cisretinoic,4-oxo trans-retinoic acid and 4-oxo trans-retinoicacid glucuronide. Elimination occurs in the urine (63%) andfeces (31%) with an elimination half-life of 40 to 120 minutes.Vitamin A toxicity is seen in nearly all patients andpresents as headache, fever, dryness of the skin, skin rash,mucositis, and peripheral edema. APL differentiation syndromesuch as that seen for arsenic trioxide also occurs.Cardiovascular effects include flushing, hypotension, CHF,stroke, and myocardial infarction have been reported butoccur only rarely. There are also several CNS and GI effectsthat have been associated with the agent as well.

일반 설명

Yellow to light-orange crystalline powder.

공기와 물의 반응

Tretinoin may be sensitive to prolonged exposure to air. Insoluble in water.

반응 프로필

Tretinoin may discolor on exposure to light. Tretinoin is extremely sensitive to exposure to light and, therefore, Tretinoin should be fully protected from light during all handling. Solutions are unstable in the presence of strong oxidizers. Tretinoin is incompatible with strong oxidizing agents. .

화재위험

Flash point data for Tretinoin are not available; however, Tretinoin is probably combustible.

생물학적 활성

Endogenous agonist for retinoic acid receptors. Also positively modulates PPAR δ receptors (K d = 17 nM). Promotes differentiation of embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro .

Clinical Use

The major toxic effect of tretinoin is erythema and irritation of the skin to which it is applied, especially if the skin is moist.This toxicity often decreases with continued therapy.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic and teratogenic data. Human mutation data reported. A human skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes. Used to treat acne and other skin problems.

Veterinary Drugs and Treatments

Topical tretinoin may be useful in treating localized follicular or hyperkeratotic disorders such as acanthosis nigrans, idiopathic nasal and footpad hyperkeratosis, callous pyodermas, or chin acne. Tretinoin’s exact mechanism of action is not well understood, but it stimulates cellular mitotic activity, increases cell turnover, and decreases the cohesiveness of follicular epithelial cells.

Purification Methods

Purify the acid by chromatography on silicic acid columns, and eluting it with a small amount of EtOH in hexane. Also dissolve it in Et2O, wash it with H2O, dry (Na2SO4), evaporate and the solid residue is recrystallised from MeOH (0.53g /3.5mL MeOH to give 0.14g) or EtOH. It also recrystallises from i-PrOH, or as the methyl ester from MeOH. UV in MeOH has max at 351nm ( 45,000). 9-Cis-acid forms yellow needles from EtOH, with m 189-190o, and its UV in MeOH has max at 343nm ( 36,500); the 13-cis-acid forms red-orange plates from i-PrOH with m 174-175o, and UV has max at 345nm ( 39,800). Store it in the dark, in an inert atmosphere, at 0o [Robeson et al. J Am Chem Soc 77 4111 1955]. [Beilstein 9 IV 2387.]

레티노산 준비 용품 및 원자재

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