Retinoic acid

概述规格名称和识别符技术文档高级数据系统学分类三维结构产品属性质检证书（CoA,COO,BSE/TSE 和分析图谱) 化学和物理性质安全和危险性（GHS）此产品的引用文献技术文档和文章引用文献溶液计算器常见问题

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为什么选择此级别

，适用于对基线干扰要求严格的色谱和分析工作流程。

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储存与运输

室温。常规运输。请查阅批次 COA 获取详细规格。

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质量文档

SDS、COA、产品数据表及规格说明书均可下载。可通过批号查询获取批次 COA。

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文献证明

在色谱分析、有机合成和交叉偶联反应领域已被 56 篇同行评审文献引用。

概述

Retinoic acid (Vitamin A acid) (GMP) 是 GMP 级别的 Retinoic acid。GMP 级别的小分子可用做细胞疗法中的辅助试剂。Retinoic acid 是 RAR 核受体的激动剂。

Retinoic acid (Vitamin A acid) (GMP) is Retinoic acid produced by using GMP guidelines. GMP small molecules works appropriately as an auxiliary reagent for cell therapy manufacture. Retinoic acid is an agonist of RAR nuclear receptors.

规格

英文名称

Retinoic acid

储存条件

室温

运输条件

常规运输

名称和识别符

EC号

206-129-0

分子类型

小分子

IUPAC Name

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid

INCHI

1S/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)/b9-6+,12-11+,15-8+,16-14+

InChi Key

SHGAZHPCJJPHSC-YCNIQYBTSA-N

Smiles

CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C

Isomeric SMILES

CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C

分子量

300.44

Beilstein号

2057223

Reaxy-Rn

2508066

Reaxys-RN link address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2508066&ln=

技术文档

📋 安全数据表 (SDS)

全面的危险、操作、储存及法规合规文件。

下载 SDS →

✅ 分析证书 (COA)

批次质量数据。输入批号以获取对应 COA。

查询 COA →

📊 产品数据表

产品规格和应用的快速参考摘要。

查看数据表 →

🔬 规格说明书

该级别的完整质量属性和验收标准。

查看规格说明 →

高级数据

系统学分类

分类树（Taxonomy Tree）

界（kingdom) 有机化合物
- 超类（Superclass) 脂质和脂质样分子
  - 类（Class) 异戊烯醇脂质
    - 亚类（Subclass）类视黄酸

界（kingdom)	有机化合物
超类（Superclass)	脂质和脂质样分子
类（Class)	异戊烯醇脂质
亚类（Subclass）	类视黄酸
中间层级节点（Intermediate Tree Nodes）	暂无
直接上位类(Direct Parent)	类视黄酸
其他上位类（Alternative Parents）	二萜类化合物中链脂肪酸甲基支链脂肪酸不饱和脂肪酸一元羧酸及其衍生物羧酸有机氧化物碳氢化合物衍生物羰基化合物
分子骨架（Molecular Framework)	脂肪族同单环化合物
取代基（Substituents）	脂肪族同单环化合物 - 支链脂肪酸 - 羰基 - 羧酰胺基 - 羧酸衍生物 - 二萜类化合物 - 脂肪酸 - 脂肪酰基 - 烃衍生物 - 中链脂肪酸 - 甲基-支链脂肪酸 - 单羧酸或其衍生物 - 有机氧化物 - 有机氧化合物 - 有机氧化合物 - 萘醌 - Retinoid skeleton - 不饱和脂肪酸
描述（Description）	该化合物属于视黄醇类有机化合物。这类化合物是3,7-二甲基-1-(2,6,6-三甲基环己-1-烯基)壬烷-1,3,5,7-四烯及其衍生物的含氧衍生物。
外部描述符（External Descriptors）	Retinoids

三维结构

交互式化学结构模型

球棍
棍棒
线框模型
空间填充
显示氢气
动画

产品属性

ALogP	6.3

化学和物理性质

熔点

180-181°C

安全和危险性（GHS）

象形图

GHS07, GHS08

信号词

危险

危险声明

H315: 引起皮肤刺激

H319: 引起严重眼睛刺激

H335: 可能引起呼吸道刺激

H360: 可能损害生育力或未出生的孩子

预防措施声明

P261: 避免吸入灰尘/烟雾/气体/雾/蒸汽/喷雾

P264: 处理后要彻底洗手。

P271: 仅在室外或通风良好的地方使用。

P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。

P321: 特殊处理（请参阅此标签上的...）。

P302+P352: 如皮肤沾染：用水充分清洗。

P304+P340: 如误吸入：将人转移到空气新鲜处，保持呼吸舒适体位。

P305+P351+P338: 如进入眼睛：用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出，取出隐形眼镜。继续冲洗。

P362+P364: 脱掉沾污的衣服，清洗后方可重新使用。

P405: 密闭存放

P403+P233: 存放在通风良好的地方。保持容器密闭。

P501: 将内容物/容器处理到。。。

P203: 使用前，获取、阅读并遵守所有安全说明。

P264+P265: 处理后彻底洗手[和…]。不要触摸眼睛。

P318: 如果暴露或担心，请就医。

P337+P317: 如果眼睛刺激持续：寻求医疗帮助。

P332+P317: 如果出现皮肤刺激：请寻求医疗帮助。

P319: 如果你感到不适，请寻求医疗帮助。

WGK Germany

RTECS

VH6475000

Merck Index

8165

个人防护装备

dust mask type N95 (US),Eyeshields,Gloves

质检证书（CoA,COO,BSE/TSE 和分析图谱)

C of A & Other Certificates(BSE/TSE, COO):

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技术文档和文章

Hedgehog信号通路

目录：技术文章

探索主题:

Hedgehog信号通路

Hedgehog Signaling

目录：技术文章

探索主题:

Hedgehog Signaling

GMP

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目录：阿拉丁试剂的规格、级别和纯度

探索主题:

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视黄醇的皮肤作用机制：从代谢激活、RAR/RXR转录调节到表皮更新与胶原稳态调节

目录：技术文章

探索主题:

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目录：技术文章

探索主题:

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乙酰基六肽-8在表情纹管理中的作用基础：SNARE复合体干预、经皮递送限制与复配思路

目录：技术文章

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目录：技术文章

探索主题:

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目录：技术文章

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目录：技术文章

探索主题:

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此产品的引用文献

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引用文献

1. Yaxin Zhao, Chao Wang, Bohang Zou, Lin Fu, Shushan Ren, Xiangyu Zhang. (2023) Design and Evaluation of Tretinoin Fatty Acid Vesicles for the Topical Treatment of Psoriasis. MOLECULES, 28 (23): (7868). [PMID:38067597] [10.3390/molecules28237868]
2. Shan Gao, Meng Liu, Dongzhu Liu, Xinru Kong, Yuelin Fang, Yingying Li, Hang Wu, Jianbo Ji, Xiaoye Yang, Guangxi Zhai. (2023) Biomimetic biomineralization nanoplatform-mediated differentiation therapy and phototherapy for cancer stem cell inhibition and antitumor immunity activation. Asian Journal of Pharmaceutical Sciences, [PMID:37915760] [10.1016/j.ajps.2023.100851]
3. Kaili Wang, Hao Chen, Si Qin, Shuhui Chen, Qian Zhang, Jiali Chen, Donghua Di, Guangyue Su, Yue Yuan. (2023) Co-delivery of pirfenidone and siRNA in ZIF-based nanoparticles for dual inhibition of hepatic stellate cell activation in liver fibrotic therapy. COLLOIDS AND SURFACES B-BIOINTERFACES, [PMID:37797465] [10.1016/j.colsurfb.2023.113567]
4. Sanli Zhang, Yan Yu, Mingyue Sheng, Xun Chen, Qi Wu, Junping Kou, Gangling Chen. (2023) Ruscogenin timing administration mitigates cerebral ischemia-reperfusion injury through regulating circadian genes and activating Nrf2 pathway. PHYTOMEDICINE, [PMID:37659295] [10.1016/j.phymed.2023.155028]
5. Li Xiang, Xin Wang, Qiangqiang Jiao, Yaru Shao, Rui Luo, Jie Zhang, Xiaotong Zheng, Shaobing Zhou, Yuping Chen. (2023) Selective inhibition of glycolysis in hepatic stellate cells and suppression of liver fibrogenesis with vitamin A-derivative decorated camptothecin micelles. Acta Biomaterialia, [PMID:37507035] [10.1016/j.actbio.2023.07.035]
6. Si Qin, Xuening Du, Kaili Wang, Da Wang, Jiani Zheng, Haiyan Xu, Xiuyan Wei, Yue Yuan. (2023) Vitamin A-modified ZIF-8 lipid nanoparticles for the therapy of liver fibrosis. INTERNATIONAL JOURNAL OF PHARMACEUTICS, [PMID:37356511] [10.1016/j.ijpharm.2023.123167]
7. Chongzhi Wu, Fu Zhang, Bowen Li, Zhiyao Li, Xin Xie, Yong Huang, Zhuo Yao, Yuan Chen, Yuan Ping, Weidong Pan. (2023) A Self-Assembly Nano-Prodrug for Combination Therapy in Triple-Negative Breast Cancer Stem Cells. Small, [PMID:37328445] [10.1002/smll.202301600]
8. Qiao Lu, Xueyang Gong, Guangtao Jia, Jingliang Wu, Siwei Liu, Ke Song, Guixiang Tian. (2023) A pH‑responsive hyaluronic acid nano‑vehicle co‑encapsulating doxorubicin and all‑trans retinoic acid for the inhibition of hepatic stellate cell‑induced tumor growth and metastasis. Molecular Medicine Reports, 28 (2): (1-11). [PMID:37326031] [10.3892/mmr.2023.13029]
9. Qi Wenxia, Wang Shenglan, Yang Heng, Luo Tingting, Zhao Feng, Han Jingtian, Zhang Jing. (2023) An albumin-based nanosystem for cocktail therapy of breast cancer amplifies the therapeutic efficacy of combination chemotherapy with photodynamic therapy. JOURNAL OF MATERIALS SCIENCE, 58 (21): (8952-8968). [10.1007/s10853-023-08590-5]
10. Sheng Mingyue, Chen Xun, Yu Yan, Wu Qi, Kou Junping, Chen Gangling. (2023) Rev-erbα agonist SR9009 protects against cerebral ischemic injury through mechanisms involving Nrf2 pathway. Frontiers in Pharmacology, [PMID:37063298] [10.3389/fphar.2023.1102567]
11. Naiying Chen, Sicheng Yao, Mingming Li, Qiuyue Wang, Xinxing Sun, Xun Feng, Yang Chen. (2023) Nonporous versus Mesoporous Bioinspired Polydopamine Nanoparticles for Skin Drug Delivery. BIOMACROMOLECULES, [PMID:36883261] [10.1021/acs.biomac.2c01431]
12. Shiyang Shen, Teng Li, Jinyi Fan, Quanlin Shao, He Dong, Xiao Xu, Ran Mo. (2022) Lipid-polymer hybrid nanoparticle with cell-distinct drug release for treatment of stemness-derived resistant tumor. Acta Pharmaceutica Sinica B, [PMID:36970217] [10.1016/j.apsb.2022.11.009]
13. Hui Jin, Ningning Jiang, Wenshu Xu, Zhongyuan Zhang, Yang Yang, Jingmin Zhang, Hui Xu. (2022) Effect of flavonoids from Rhizoma Drynariae on osteoporosis rats and osteocytes. BIOMEDICINE & PHARMACOTHERAPY, [PMID:36076521] [10.1016/j.biopha.2022.113379]
14. Rong Zhang, Wei Jia. (2022) Authenticity and traceability of goat milk: Molecular mechanism of β-carotene biotransformation and accessibility. FOOD CHEMISTRY, [PMID:35483296] [10.1016/j.foodchem.2022.133073]
15. Wang Yufeng, Wang Chunxu, Zuo Nan, Yang Hao, Fang Shaohong, Shi Jialan. (2022) Extracellular Traps Increase Burden of Bleeding by Damaging Endothelial Cell in Acute Promyelocytic Leukaemia. Frontiers in Immunology, [PMID:35479063] [10.3389/fimmu.2022.841445]
16. Guohua Yao, Muhammad Muhammad, Jiajiang Zhao, Jianguo Liu, Qing Huang. (2022) DFT-based Raman spectral study of astaxanthin geometrical isomers. Food Chemistry: Molecular Sciences, [PMID:35769397] [10.1016/j.fochms.2022.100103]
17. Yupeng Liu, Fangying Yu, Suhuan Dai, Tingting Meng, Yun Zhu, Guoxi Qiu, Lijuan Wen, Xueqing Zhou, Hong Yuan, Fuqiang Hu. (2021) All-Trans Retinoic Acid and Doxorubicin Delivery by Folic Acid Modified Polymeric Micelles for the Modulation of Pin1-Mediated DOX-Induced Breast Cancer Stemness and Metastasis. MOLECULAR PHARMACEUTICS, [PMID:34579532] [10.1021/acs.molpharmaceut.1c00220]
18. Hang Hu, Defeng Xu. (2021) Co-delivery of docetaxel and retinoic acid by poly (ethylene glycol)-retinoic acid conjugates based micelles for synergistic prostate cancer therapy. Micro & Nano Letters, 16 (6): (336-343). [10.1049/mna2.12036]
19. Jiang Ying, Song Hanbing, Jiang Ling, Qiao Yu, Yang Dan, Wang Donghua, Li Ji. (2020) Silybin Prevents Prostate Cancer by Inhibited the ALDH1A1 Expression in the Retinol Metabolism Pathway. Frontiers in Cell and Developmental Biology, [PMID:32984354] [10.3389/fcell.2020.574394]
20. Ken Zhao, Jie Liu, Gang Dong, Huan Xia, Pingan Wang, Xuan Xiao, Zhen Chen. (2020) Preliminary research on the effects and mechanisms of umbilical cord‑derived mesenchymal stem cells in streptozotocin‑induced diabetic retinopathy Corrigendum in /10.3892/ijmm.2020.4708. INTERNATIONAL JOURNAL OF MOLECULAR MEDICINE, 46 (2): (849-858). [PMID:32626946] [10.3892/ijmm.2020.4623]
21. Chengyan Sun, Ning Jia, Rui Li, Ze Zhang, Yi Zhong, Kun Han. (2020) miR-143-3p inhibition promotes neuronal survival in an Alzheimer’s disease cell model by targeting neuregulin-1. FOLIA NEUROPATHOLOGICA, 58 (1): (10-21). [PMID:32337953] [10.5114/fn.2020.94002]
22. Hu Hang, Wang Chong, Zhang Rong, Xiao Chen, Lai Chao, Li Zifu, Xu Defeng. (2020) Branched worm-like nanoparticles featured with programmed drug release for synergistic castration-resistant prostate cancer therapy. JOURNAL OF MATERIALS SCIENCE, 55 (16): (6992-7008). [10.1007/s10853-020-04495-9]
23. Song Lin, Yao Lifen, Zhang Limei, Piao Zhongyuan, Lu Yichan. (2020) Schizandrol A protects against Aβ1–42-induced autophagy via activation of PI3K/AKT/mTOR pathway in SH-SY5Y cells and primary hippocampal neurons. NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 393 (9): (1739-1752). [PMID:31900522] [10.1007/s00210-019-01792-2]
24. Qing-qing Xia, Ling-min Zhang, Ying-ying Zhou, Ya-lin Wu, Jie Li. (2019) All-trans-retinoic acid generation is an antidotal clearance pathway for all-trans-retinal in the retina. Journal of Zhejiang University-SCIENCE B, [PMID:31749343] [10.1631/jzus.B1900271]
25. Chao Guo, Junrong Zhu, Jingwen Wang, Jialin Duan, Shanbo Ma, Ying Yin, Wei Quan, Wei Zhang, Yue Guan, Yi Ding, Aidong Wen, Yingdong Zhang. (2019) Neuroprotective effects of protocatechuic aldehyde through PLK2/p-GSK3β/Nrf2 signaling pathway in both in vivo and in vitro models of Parkinson's disease. Aging-US, [PMID:31697645] [10.18632/aging.102394]
26. Lihong Ruan, Ningning Jiang, Fengyang Guo, Hui Xu, Jingmin Zhang, Jingchun Sun. (2019) The antiresoptive effects of recombinant Lingzhi-8 protein against retinoic acid-induced osteopenia. EUROPEAN JOURNAL OF PHARMACOLOGY, [PMID:31542486] [10.1016/j.ejphar.2019.172669]
27. Lumei Chi, Dan Jiao, Guangxian Nan, Honghua Yuan, Jing Shen, Yu Gao. (2019) miR-9-5p attenuates ischemic stroke through targeting ERMP1-mediated endoplasmic reticulum stress. ACTA HISTOCHEMICA, [PMID:31500865] [10.1016/j.acthis.2019.08.005]
28. Cui Huang, Jing Ma, Bai‑Xiang Li, Yan Sun. (2019) Wnt1 silencing enhances neurotoxicity induced by paraquat and maneb in SH‑SY5Y cells. Experimental and Therapeutic Medicine, 18 (5): (3643-3649). [PMID:31602242] [10.3892/etm.2019.7963]
29. Tingting Luo, Jingtian Han, Feng Zhao, Xiaohong Pan, Baocheng Tian, Xiujuan Ding, Jing Zhang. (2019) Redox-sensitive micelles based on retinoic acid modified chitosan conjugate for intracellular drug delivery and smart drug release in cancer therapy. CARBOHYDRATE POLYMERS, [PMID:30981373] [10.1016/j.carbpol.2019.03.064]
30. Yanqiu Zhang, Lianjun Peng, Jiahui Chu, Ming Zhang, Lizhu Sun, Bin Zhong, Qiyong Wu. (2018) pH and redox dual-responsive copolymer micelles with surface charge reversal for co-delivery of all-trans-retinoic acid and paclitaxel for cancer combination chemotherapy. International Journal of Nanomedicine, [PMID:30410335] [10.2147/IJN.S179046]
31. Jia Jiao, Hongshuai Wu, Fanghui Chen, Renjie Chen, Baiwang Sun, Mingliang Wang. (2018) Delivery of coumarin-containing all-trans retinoic acid derivatives via targeted nanoparticles encapsulating indocyanine green for chemo/photothermal/photodynamic therapy of breast cancer. NEW JOURNAL OF CHEMISTRY, 42 (11): (8805-8814). [10.1039/C8NJ00578H]
32. Yuming Yang, Caixia Yue, Yu Han, Wei Zhang, Aina He, Chunlei Zhang, Ting Yin, Qian Zhang, Jingjing Zhang, Yao Yang, Jian Ni, Jielin Sun, Daxiang Cui. (2016) Tumor-Responsive Small Molecule Self-Assembled Nanosystem for Simultaneous Fluorescence Imaging and Chemotherapy of Lung Cancer. ADVANCED FUNCTIONAL MATERIALS, 26 (47): (8735-8745). [10.1002/adfm.201601369]
33. Jing Zhang, Jian Han, Xiuli Zhang, Jing Jiang, Maolei Xu, Daolai Zhang, Jingtian Han. (2015) Polymeric nanoparticles based on chitooligosaccharide as drug carriers for co-delivery of all-trans-retinoic acid and paclitaxel. CARBOHYDRATE POLYMERS, [PMID:26050884] [10.1016/j.carbpol.2015.04.036]
34. Juan Yang, Nana Wu, Jie Peng, Xiaoquan Yang, Jian Guo, Shouwei Yin, Jinmei Wang. (2015) Prevention of retinoic acid-induced osteoporosis in mice by isoflavone-enriched soy protein. JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 96 (1): (331-338). [PMID:25645024] [10.1002/jsfa.7098]
35. Taihang Zhou, Fen Qiao, Sen Qian, Shoaib Muhammad, Haitao Li, Yanzhen Liu. (2024) CdTe QDs@SiO2 composite material for efficient photocatalytic degradation of tetracycline composites. Green Chemical Engineering, [10.1016/j.gce.2024.01.004]
36. Qida Hu, Fu Zhang, Bowen Li, Piaopiao Jin, Junming Huang, Zhuo Yao, Xinyu Zhao, Shiyi Shao, Meng Wang, Yuan Ping, Tingbo Liang. (2025) Engineered a Gemcitabine Nano-Prodrug Targeting Desmoplastic Pancreatic Tumor with Dual Enhancement of Penetration Dynamics. Small, [PMID:40007057] [10.1002/smll.202410629]
37. Li Xiang, Xianjing Xiang, Qiangqiang Jiao, Yu Luo, Guodong Zeng, Wenhui Zhang, Yuting Qin, Yuping Chen. (2025) Inhibition of HSC proliferation and hepatic fibrogenesis with Erythrocyte membrane coated Doxorubicin/Black phosphorus nanosheets. INTERNATIONAL JOURNAL OF PHARMACEUTICS, [PMID:40015579] [10.1016/j.ijpharm.2025.125403]
38. Chunfei Zhong, Xinyan Li, Fan Zhang, Ning Liu, Jiewei Deng, Yunyun Yang, Tiangang Luan. (2024) Rapid and sensitive determination of bongkrekic acid with molecularly imprinted polymer-coated wooden-tip electrospray ionization mass spectrometry. Advances in Sample Preparation, [10.1016/j.sampre.2024.100137]
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