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3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

HCID 5538
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
78996-15-3
표준 SMILES
CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(=O)O
InChIKey
SHGAZHPCJJPHSC-UHFFFAOYSA-N
분자식
C20H28O2
평균 분자량
300.4 g/mol
단동위원소 질량
300.20893013

개요

Retinoic acid is a retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified). It has a role as a human metabolite. It is a retinoid and an alpha,beta-unsaturated monocarboxylic acid. It is a conjugate acid of a retinoate.

이름 및 식별자

우선 이름
3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
IUPAC
3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
영어명
SHGAZHPCJJPHSC-GOWYKSNKSA-N
분자식
C20H28O2
분자량
300.44

이름 및 동의어

3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acidRefChem:106615311-cis Retinoic Acid3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acidTretinoina (INN-Spanish)Tretinoina [INN-Spanish]Isotretinoin EP Impurity CAvita (0.025% gel)retinylpalmitats1653LGD 100057Spectrum_001676
이름 더 보기
D5-IsotretinoinRetinoic acid-dRetinoic Acid-d5SHGAZHPCJJPHSC-GOWYKSNKSA-NRetinoic-4,4,18,18,18-d5 acidIsotretinoin D5Q: What is Isotretinoin D5 Q: What is the CAS Number of Isotretinoin D5 Q: What is the storage condition of Isotretinoin D5 Q: What are the applications of Isotretinoin D5
SpecPlus_000696Prestwick0_000256Prestwick0_000257Prestwick1_000256Prestwick1_000257Spectrum2_001983Spectrum3_001793Spectrum4_000901

물성

구조 계산 물성보충 중

XLogP
6.3
극성 표면적
37.3 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
2
회전 가능 결합 수
5
무거운 원자 수
22
형식 전하
0
복잡도
567

실험 및 물리화학적 성질

LogP6.3

물리화학적 성질

저장 조건
-80 °C · Store at -80°C
용해도
메탄올 에 용해됨
물리적 상태
고체
색상
White to off-white

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

독성 정보

Exposure Routes1-31% (topical)
Toxicity Summary · 1건

Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

화학 및 산업

약리 정보

Metabolism/MetabolitesHepatic Half Life: 0.5-2 hours

용도 및 제조

Uses · 1건

For the the induction of remission in patients with acute promyelocytic leukemia (APL), French-American-British (FAB) classification M3 (including the M3 variant); For the topical treatment of acne vulgaris, flat warts and other skin conditions (psoriasis, ichthyosis congenita, icthyosis vulgaris, lamellar icthyosis, keratosis palmaris et plantaris, epidermolytic hyperkeratosis, senile comedones, senile keratosis, keratosis follicularis (Darier's disease), and basal cell carcinomas.); For palliative therapy to improve fine wrinkling, mottled hyperpigmentation, roughness associated with photodamage.

응용 분야 · 2건

개요13-cis Retinoic acid-d5 is intended for use as an internal standard for the quantification of 13-cis retinoic acid by GC- or LC-MS. 13-cis Retinoic acid is a naturally occurring retinoid that inhibits retinol oxidation and dehydrogenation of 17β-hydroxy steroids.

용도An endogenous retinoic acid isomer, which is capable of binding to both retinoic acid receptors (RAR) and retinoid X receptors (RXR). A biologically active ligand for members of the RAR and RXR subfamilies, implying that it may play a critical role in regulating retinoid-responsive pathways.

관련 반응

8건
반응 기록 만들기
HRID 140142 반응식
HRID 140142생성물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 171983 반응식
HRID 171983반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 179424 반응식
HRID 179424반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 184668 반응식
HRID 184668생성물로반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 1142109 반응식
HRID 1142109생성물로Training data from https://doi.org/10.1039/C8SC04228D (7/10)
HRID 1149157 반응식
HRID 1149157생성물로Training data from https://doi.org/10.1039/C8SC04228D (7/10)
HRID 1228653 반응식
HRID 1228653반응물로Training data from https://doi.org/10.1039/C8SC04228D (5/10)
HRID 1238402 반응식
HRID 1238402생성물로반응물로Training data from https://doi.org/10.1039/C8SC04228D (5/10)

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데이터베이스 식별자

CAS
78996-15-3
PubChem CID
5538
ChEMBL
CHEMBL1235644
ChEBI
CHEBI:26536