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Product name: Bixin
Synonym name: 6-Methyl hydrogen (9Z)-6,6'-diapocarotene-6,6'-dioate
Catalogue No.: BP2092
Cas No.: 6983-79-5
Formula: C25H30O4
Mol Weight: 394.511
Botanical Source:
Type of Compound:
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Bixin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
63.6000
5.2160
2.7279
.0065
2.9523
5.5299
Low
94.5966
3.4461
Yes
Yes
Yes
No
No
No
0.3
No
Yes
Yes
Yes
Bixin, also known as annatto orange, is a carotenoid natural product mainly found in the seeds of the annatto (Bixa orellana). As a natural pigment, rosewood has been widely used since ancient times in food, cosmetics, and traditional medicine. In recent years, with the development of natural product pharmacology and molecular biology technologies, the biological activity and potential medicinal value of rosewoodin have gradually attracted attention. Numerous studies have shown that rosewood not only possesses significant antioxidant, anti-inflammatory, and antitumor activities, but can also regulate apoptosis, inhibit fibrosis, and improve heart function through various molecular mechanisms, demonstrating broad therapeutic potential.
This paper aims to systematically review the chemical structure and physicochemical properties of rosewoodin, its plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation and pharmacokinetic characteristics, and to explore its clinical application prospects and future research directions, providing theoretical basis and reference for related research in the field of natural product pharmacology.
Bixin (Erythrocylin) has the chemical name (C25H30O4), molecular weight 394.5110, CAS number 6983-79-5. Its structure belongs to the carotenoid family, specifically a diterpene compound containing a conjugated double bond system. The molecular structure of rosewoodin consists of a long-chain conjugated double bond system and two carboxyl functional groups, giving it strong light absorption and antioxidant properties.
In terms of physicochemical properties, the LogP value of rosewoodin is 5.2160, indicating high lipid solubility but extremely low water solubility (0.0065 mg/mL), which also limits its solubility and bioavailability in the aqueous phase. Its topological pole surface area (TPSA) is 63.6 Ų, indicating that the molecule has certain polarity, which facilitates interaction with biological targets. Erygin has low blood-brain barrier permeability, suggesting limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of erygin cardiotoxicity. Ames test results showed that its mutagenicity was extremely low (0.3) and it had good safety.
Rosewoodin mainly comes from the seeds of the annatto tree (Bixa orellana). The annatto tree belongs to the Malvaceae family, widely distributed in tropical America and parts of Asia. Its seed husk is rich in rosewood, which has traditionally been used as a natural pigment and dye.
There are various methods for extracting rosewood, commonly including organic solvent extraction, supercritical fluid extraction, and enzyme-assisted extraction. Traditional extraction mostly uses organic solvents such as ethanol, ethyl acetate, or hexane, and crude rosewoodin extracts are obtained through extraction and concentration. Supercritical carbon dioxide extraction has become a research hotspot in recent years due to its green and environmentally friendly nature and efficient selectivity. In addition, to improve extraction efficiency and purity, researchers also used column chromatography, thin-layer chromatography, and high-performance liquid chromatography (HPLC) for purification and quantitative analysis.
Roseginin has significant antioxidant effects. Its conjugated double bond structure enables it to effectively scavenge free radicals, inhibit the generation of reactive oxygen species (ROS), and reduce oxidative stress damage. In vitro experiments have shown that redwood can enhance the activity of superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GPX1), protecting cells from oxidative damage. In animal models, rosewood significantly reduces levels of lipid peroxidation products (such as malondialdehyde, MDA), increases antioxidant enzyme expression, and plays a protective role in the heart, liver, and nervous tissue.
Roseginin demonstrates good anti-inflammatory effects by inhibiting the production and release of various inflammatory mediators. It can downregulate the nuclear factor κB (NF-κB) signaling pathway, reducing the expression of pro-inflammatory cytokines such as tumor necrosis factor α (TNF-α), interleukin-6 (IL-6), and nitric oxide (NO), thereby alleviating inflammatory responses. Related studies have shown that redwoodin significantly reduces tissue inflammation and cellular infiltration in models of inflammatory diseases, suggesting its potential as an anti-inflammatory drug.
The ability of rosewood to induce cancer cell apoptosis has been confirmed by multiple in vitro and in vivo studies. By activating mitochondrial pathways, it regulates the Bcl-2 family proteins, promotes cytochrome C release, and activates caspases cascades, inducing programmed tumor cell death. In addition, redwood can inhibit tumor cell proliferation, migration, and invasion, regulate cell cycle-related proteins, and demonstrate multi-target anti-tumor mechanisms. Some studies have also found that rosegin can enhance the sensitivity of chemotherapy drugs and has potential adjunctive therapeutic value.
Rosewoodin improves heart dysfunction by inhibiting fibrosis, inflammation, and oxidative stress in heart tissue. It can reduce collagen deposition, regulate matrix metalloproteinase (MMP1, MMP3) activity, and alleviate myocardial remodeling. Erygin also activates the nuclear factor 2-related factor 2 (Nrf2) signaling pathway, promotes the expression of antioxidant enzyme genes, and protects myocardial cells from oxidative damage. Animal experiments have shown that redwoodin significantly improves cardiac function in models of heart failure and ischemia-reperfusion injury, suggesting its potential in cardiovascular disease prevention and treatment.
The multiple pharmacological effects of rosewoodin depend on its regulation of various molecular targets. Its main mechanisms of action include:
Antioxidant mechanism
Rosewoodin activates the Nrf2 (NFE2L2) signaling pathway, promoting the expression of downstream antioxidant enzymes such as SOD1, SOD2, CAT, GPX1, and HMOX1, enhancing cellular antioxidant defenses, reducing ROS production, and protecting cells from oxidative damage.
Anti-inflammatory mechanism
Erygin inhibits the NF-κB signaling pathway, reduces the release of pro-inflammatory factors TNF-α, IL-6, and nitric oxide, and lowers inflammatory responses. It may also further inhibit the expression of inflammatory mediators by regulating the MAPK pathway.
Antitumor mechanism
Redwood induces cancer cell apoptosis, involving mitochondrial pathway activation and regulation of caspase family proteins. It inhibits cyclins and related signaling pathways, blocking tumor cell proliferation and metastasis.
Anti-fibrotic mechanism
By regulating MMP1 and MMP3 activities, erygin inhibits collagen deposition, reduces tissue fibrosis, and improves organ function.
Other targets
Roseginin also regulates enzymes such as tyrosinase (TYR), which may affect pigment metabolism and related physiological processes.
Drug development evaluation of rosewoodin shows that it has certain advantages and challenges. Its molecular weight of 394.5110 and high lipid solubility (LogP 5.2160) facilitate cell membrane penetration, but extremely low water solubility limits its oral bioavailability. Additionally, the low permeability of the redwood-brain barrier reduces the potential risk of toxicity in the central nervous system, but at the same time limits its application in neurological diseases.
In terms of safety, erygin does not have significant hERG channel inhibitory effects, has low mutagenicity, and has a solid safety foundation. Pharmacokinetic studies show that roseginin is mainly metabolized in the liver in the body, but the activity and pathways of biotransformation products still require further elucidation.
To overcome the issues of poor water solubility and low bioavailability, in recent years, researchers have attempted strategies such as nanocarriers, liposome encapsulation, and structural modification to enhance the solubility and targeting of rosewoodin, thereby promoting its clinical translation.
With its remarkable antioxidant, anti-inflammatory, and antitumor activities, rosewoodin demonstrates broad clinical application potential. Its applications are particularly prominent in cardiovascular diseases, tumor treatment, and chronic inflammatory diseases. In the future, as formulation technology advances, the bioavailability and targeting of rosewood are expected to be significantly improved, driving its transformation into clinical drugs.
Moreover, as a natural pigment, the safety advantage of rosewood provides a solid foundation for its application in functional foods, nutritional supplements, and adjunct therapies. Further clinical trials and pharmacological mechanism studies will help clarify the therapeutic window, dosage safety, and long-term efficacy of rosewoodin.
Future research should focus on the metabolic mechanisms of rosewoodin, drug interactions, and multi-target synergistic effects, combining modern drug design with nanotechnology to develop efficient, safe, and well-targeted new derivative drugs that contribute new therapeutic strategies to the field of natural product pharmacology.
As an important carotenoid in annatto seeds, rosewood has rich pharmacological activity and good safety, making it a hot topic in natural product pharmacological research. Its multiple biological effects—antioxidant, anti-inflammatory, anti-tumor, and cardioprotective—provide new ideas for the prevention and treatment of various diseases. Although its poor water solubility and low bioavailability limit clinical application, modern formulation technology and molecular modification have broad prospects for drug development of rosewoodin.
In the future, systematic and in-depth pharmacological mechanism research, optimized pharmacokinetic characteristics, and rigorous scientific clinical evaluation will be key to promoting the transformation of rosewoodin from a natural product into a clinical drug. Research on rosewood not only enriches the understanding of the biological functions of carotenoids, but also provides valuable examples and insights for the development of natural product pharmacology.
Shenshuai
Wenjing
Hedandan
