基本情報
- CAS
79-81-2- 標準SMILES
CCCCCCCCCCCCCCCC(=O)OC/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C- InChIKey
VYGQUTWHTHXGQB-FFHKNEKCSA-N- 分子式
- C36H60O2
- 平均分子量
- 524.9 g/mol
- 単同位体質量
- 524.45933116
概要
All-trans-retinyl palmitate is an all-trans-retinyl ester obtained by formal condensation of the carboxy group of palmitic (hexadecanoic acid) with the hydroxy group of all-trans-retinol. It is used in cosmetic products to treat various skin disorders such as acne, skin aging, wrinkles, dark spots, and also protect against psoriasis. It has a role as an antioxidant, a human xenobiotic metabolite and an Escherichia coli metabolite. It is a retinyl palmitate and an all-trans-retinyl ester. It is functionally related to an all-trans-retinol.
名称と識別子
- 優先名称
- Retinol Palmitate
- IUPAC
- [(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
- 現地名
- ビタミン A パルミテート,油性
- 英語名
- Vitamin A palmitate
- 分子式
- C36H60O2
- 分子量
- 524.86
名称と別名
retinyl palmitateVITAMIN A PALMITATE79-81-2Retinol palmitateRetinol, hexadecanoateall-trans-Retinyl palmitateArovitOptovit-ARetinyl hexadecanoateVitamin A SolubilizedDTXSID1021241[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
名称をさらに表示
パルミチン酸レチノールビタミン A パルミテート,油性ビタミンA脂肪酸（C＝2～19）エステルビタミンAパルミタート, 油性パルミチン酸レチノール標準液ビタミンAパルミテートパルミチン酸ALL-TRANS-レチニルパルミチン酸レチニルレチノールパルミチン酸エステルレチノールパルミチン酸エステル (JP17)ビタミンAパルミタートチョコラAレチノールパルミタートビタミンAパルミチン酸エステル(2E,4E,6E,8E)-3,7-ジメチル-9-(2,6,6-トリメチルシクロヘキサ-1-エン-1-イル)ノナ-2,4,6,8-テトラエン-1-イル ヘキサデカノアートレチノールヘキサデカノアートビタミンA1パルミチン酸エステルレチニルパルミタートVitamin a Palmitate OilVitamin A Palmitate Powder
物性
構造計算による物性
- XLogP
- 13.6
- 極性表面積
- 26.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 21
- 重原子数
- 38
- 形式電荷
- 0
- 複雑度
- 803
実験および物理化学的性質
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]
Cosmetics
Cosmetic ingredients (Retinyl Palmitate) -> CIR (Cosmetic Ingredient Review)
Skin conditioning
Food AdditivesCOLOR OR COLORING ADJUNCT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point28.5 °C
Physical DescriptionSolid
物理化学的性質
- 融点
- 28 · 28-29℃
- 沸点
- 546.51 °C · 546.51°C (rough estimate)
- 比重(密度)
- 0.9668 · 0.9668 (rough estimate)
- 屈折率
- 1.525 · 1.5250 (estimate)
- 闪点
- 194 ℃ · 194℃
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- クロロホルム（微量）、酢酸エチル（微量）、メタノール（微量）
- 外見
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 8.4% (54 of 643) of reports.
Danger
H315 (19%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P264, P273, P280, P302+P352, P318, P321, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 643 reports by companies from 30 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Retinol, hexadecanoate
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 13-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13687
Retinyl palmitate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (19%)
毒性情報
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Vitamin A palmitate
vLess-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
安全データ
- F
- 8-10-23
- wgk
- 3
- tsca
- TSCA listed
- rtecs
化学と産業
薬理情報
MeSH Pharmacological Classification
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular
Metabolite PathwaysRetinol Metabolism
用途と製造
UsesCIR ingredient: Retinyl Palmitate
Household ProductsInformation on 131 consumer products that contain Retinyl palmitate in the following categories is provided:
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationRetinol, hexadecanoate: ACTIVE
応用分野
用途ビタミンA定量用標準品。
使用vitamin A palmitate is known as a skin “normalizer.” It acts as an antikeratinizing agent, helping the skin stay soft and plump, and improving its water-barrier properties. Because of its impact on the skin’s water-barrier properties, it is useful against dryness, heat, and pollution. It is also an anti-oxidant and is suggested for use in sunscreens. Clinical studies with vitamin A palmitate indicate a significant change in skin composition, with increases in collagen, DnA, skin thickness, and elasticity. Vitamin A palmitate’s stability is superior to retinol.
Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards.Retinyl palmitate belongs to a category of compounds called retinoids, which are chemically similar to vitamin A. It exhibits a beneficial effect on vision, skin and immune function, inhibits cell proliferation and prevents cancer. It is an important dietary as well as a therapeutic compound.
関連反応
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化合物ノート
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