Product name: 3-Hydroxysalidroside-4-O-glucopyranoside
Synonym name: Hydroxytyrosol-1,4-O-β-diglucopyranoside
Catalogue No.: BP2388
Cas No.:
Formula: C₂₀H₃₀O₁₃
Mol Weight: 478.447
Botanical Source:
Type of Compound: Phenols

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.

NMR of 3-Hydroxysalidroside-4-O-glucopyranoside

HPLC of 3-Hydroxysalidroside-4-O-glucopyranoside

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Exploration of the Chemical, Pharmacological, and Pharmaceutical Prospects of 3-hydroxysalidrosin-4-O-glucoside, a New Star of Natural Products

1. Overview

3-Hydroxysalidroside-4-O-glucopyranoside is a traditional medicinal plant derived from Rhodiola rosea Rhodiola rosea（Rhodiola rosea）Natural products of phenylethanoid glycosides obtained through separation. As a structural analogue of salidroside, this compound introduces a hydroxyl group at position 3 of the phenylethanolic glycoside nucleus and connects an additional glucose group through a glycosidic bond at position 4, forming a unique dual glycosidic structure. This structural modification may not only significantly alter its physicochemical properties, but also endow it with unique biological activity distinct from salidroside. Rhodiola, as a famous "adaptogen" herb, has been used in traditional medicine for hundreds of years for anti fatigue, anti hypoxia, enhancing immunity and neuroprotection. The research on its core active ingredient, salidroside, has been relatively in-depth. However, the research on derivative glycosides such as 3-hydroxysalidrosin-4-O-glucoside is still in its infancy and belongs to a promising "new member" in the complex chemical composition system of Rhodiola rosea. At present, systematic research data on this compound, including its precise molecular formula, molecular weight, detailed pharmacological targets, and preclinical drug parameters, are still scarce in public databases (such as CAS number, target information, etc. are not clear), which not only indicates its novelty, but also suggests huge exploration space. This article aims to systematically review and prospectively analyze the structural characteristics, potential mechanisms of action, potential drug applications, and future research directions of this compound based on the existing knowledge framework of natural product chemistry and pharmacology.

2. Chemical structure and physicochemical properties

3-hydroxysalidrosin-4-O-glucoside belongs to the phenylethanoid glycoside class of compounds. Its basic skeleton consists of three parts:Phenylethanolic glycoside(Tyrol derivatives), one Glucose based And an additional one 4-O-linked glucose group The key structural features are:
1. 3-hydroxylation Introducing a phenolic hydroxyl group at position 3 of the benzene ring enhances its ability to act as a hydrogen bond donor and may improve its antioxidant activity, as the phenolic hydroxyl group is a key functional group for scavenging free radicals.
2. 4-O-glucosylation A disaccharide chain is formed by connecting a second pyranose glucose group through an oxygen glycosidic bond at position 4 of the benzene ring. This greatly increases the molecular weight Polarity and Water solubility。

Although the exact molecular formula and molecular weight of the compound have not been disclosed yet, we can make reasonable speculations based on its parent nucleus structure. The molecular weight of salidroside (C14H20O7) is 300.30. 3-hydroxysalidrosin-4-O-glucoside adds one hydroxyl group (+16 Da) and one glucose group (C6H10O5,+162.14 Da) to salidroside. Therefore, it Speculation on molecular formula Perhaps for C20H30O13，Speculation on molecular weight approximately 478.45 Da。

Physical and chemical property analysis：
- solubility Due to the presence of two highly hydrophilic glucose groups and multiple hydroxyl groups, this compound is expected to have Extremely high water solubility Has poor solubility in fat soluble solvents.
- LogP (Fat Water Partition Coefficient)This is a key parameter for measuring the lipophilicity of compounds. The measured LogP value of salidroside is approximately -1.0 to -0.5, indicating that it belongs to hydrophilic compounds. 3-hydroxysalidrosin-4-O-glucoside has added more polar groups, which Speculation that the LogP value will be lower (possibly<-2.0)This indicates that its ability to cross the lipid bilayer membrane of cells will be weaker.
- Topological Polarity Surface Area (TPSA)TPSA is closely related to the membrane permeability and bioavailability of compounds. The TPSA of salidroside is approximately 120 Å ². The additional glucose and hydroxyl groups will significantly increase the number of hydrogen bond acceptors and donors Speculation that TPSA may exceed 200 Å ²This is usually not conducive to passive transmembrane diffusion, especially through the blood-brain barrier (BBB).
- Stability As an O-glycoside, it may undergo hydrolysis in acidic environments and may also undergo deglycosylation metabolism under the action of gut microbiota.

3. Plant sources and traditional applications

The only known plant source of 3-hydroxysalidrosin-4-O-glucoside is Rhodiola rosea（Rhodiola rosea L.）It belongs to the Crassulaceae family. Rhodiola mainly grows in extreme environments with high altitude, oxygen deficiency, and strong ultraviolet radiation, such as near the Arctic Circle, high-altitude mountain ranges in Asia and Europe (such as the Himalayas and Alps). This harsh growth environment forces plants to synthesize a series of secondary metabolites with strong stress protection effects, among which phenylethanolic glycosides are an important class.

The medicinal history of Rhodiola rosea dates back to ancient times. In the traditional medical system, its application has significant "adaptogen" characteristics:
- Traditional Chinese Medicine Rhodiola rosea (also known as "Rose Rhodiola rosea") is used for medicinal purposes in its roots and rhizomes. It is sweet, astringent, and cold in nature, and belongs to the lung and heart meridians. Commonly used in Tonifying Qi and Promoting Blood Circulation, Tonifying Meridians and Relieving Asthma It is mainly used for treating diseases such as qi deficiency and blood stasis, fatigue and asthma, chest tightness and heartache, and is highly consistent with modern research on anti fatigue, anti hypoxia, and cardiovascular protection effects.
- Nordic and Russian Traditional Medicine Long term use for enhancing Physical strength, endurance, and fatigue resistance To help the body adapt to cold and high altitude environment, and to treat neurasthenia, depression and infectious diseases.
- Tibetan medicine Rhodiola rosea is regarded as a precious medicinal herb, used to treat "lung" disease (equivalent to traditional Chinese medicine's qi and blood imbalance, neurasthenia) and "chiba" disease (heat syndrome), emphasizing its role in balancing the body and enhancing adaptability.

Although traditional applications do not directly target the single component of 3-hydroxysalidrosin-4-O-glucoside, they provide a profound empirical medical background and clear direction for its pharmacological activity research - that is, this compound is likely to participate in mediating the overall anti stress, neuroprotective, and cardiovascular protective effects of salidroside.

4. Pharmacological activity and mechanism of action (based on structural analogy and potential pathway analysis)

Although there is a lack of direct target research data for 3-hydroxysalidrosin-4-O-glucoside, we can start from the common pharmacological mechanisms of its parent compounds salidroside and phenylethanoid glycosides, combined with their unique chemical structures, to make reasonable activity predictions and mechanism deductions.

4.1 Prediction of core potential pharmacological activity

1. Strong antioxidant and anti-inflammatory activity：

   • Structural Foundation The 3-hydroxy group on the benzene ring is a potent electron donor that can effectively neutralize reactive oxygen species (ROS) and reactive nitrogen species (RNS). Although additional glucose groups do not directly participate in antioxidant activity, they may affect the reactivity of phenolic hydroxyl groups through spatial effects or affect their distribution within cells through targeted delivery.
   • Mechanism deduction This compound may directly scavenge free radicals and upregulate the endogenous antioxidant system of cells (such as activation)Nrf2/ARE pathway Inducing the expression of heme oxygenase-1, superoxide dismutase, and glutathione peroxidase to exert antioxidant effects. In terms of inflammation, it may be achieved through inhibition NF-κB and MAPK Activation of signaling pathways reduces the production of pro-inflammatory factors such as TNF - α, IL-6, IL-1 β.

2. Neuroprotection and antidepressant/anti anxiety potential：

   • The core neuroprotective mechanism of salidroside involves regulating the levels of monoamine neurotransmitters such as serotonin, dopamine, and norepinephrine, inhibiting neuronal apoptosis, and promoting the expression of neurotrophic factors.
   • 3-hydroxysalidrosin-4-O-glucoside may exert its effects through a similar pathway. Its higher polarity may limit its direct penetration through the blood-brain barrier, but there are the following possibilities:
     • Prodrug or metabolic activation After hydrolysis to remove some sugar groups in the body, active metabolites with lower polarity and easier brain entry (such as 3-hydroxysalidroside or tyrosol) are generated.
     • Acting on the peripheral central connecting axis: By adjusting Hypothalamic pituitary adrenal axis (HPA axis) Function, reduce cortisol levels, indirectly produce anti stress and improve mood effects. HPA axis dysfunction is a core pathological link in depression and chronic stress.
     • Protecting the blood-brain barrier Through its anti-inflammatory and antioxidant effects, it reduces damage to the endothelial cells of the blood-brain barrier, indirectly promoting the homeostasis of the central nervous system.

3. Cardiovascular protective effect：

   • Possible protection of vascular endothelial cells through antioxidant stress, promotion of nitric oxide (NO) production, and vasodilation of blood vessels; Inhibit abnormal proliferation of vascular smooth muscle cells; And anti cardiomyocyte apoptosis and ischemia/reperfusion injury. Its function may be related to regulation PI3K/Akt and AMPK Related to cell survival signaling pathways.

4. Anti fatigue and enhanced energy metabolism：

   • The typical manifestation of adaptive effects. Possible by increasing muscle and liver function Glycogen reserve Promote mitochondrial biosynthesis and function (activation)PGC-1αPathway), improve ATP generation efficiency, and reduce the accumulation of lactate and ammonia produced by exercise, thereby delaying fatigue.

4.2 Scientific explanation of the association between potential targets and diseases

Although there is currently no direct target data, based on similar studies, the following molecular targets may be related to it:
- Kinases and signaling proteins AMPK (main regulator of energy metabolism), Akt (key protein in cell survival pathway), ERK1/2 (signal of cell proliferation and differentiation).
- transcription factor Nrf2 (antioxidant response master factor), NF - κ B (inflammatory response master factor), CREB (related to neuroplasticity and memory).
- enzyme Monoamine oxidase (MAO, neurotransmitter metabolizing enzyme) and acetylcholinesterase (AChE, related to cognitive function).
- receptor May indirectly regulate the sensitivity of glucocorticoid receptors (GR) and affect the HPA axis.

Related diseases Its potential pharmacological activity points to a range of chronic diseases associated with oxidative stress, inflammation, and metabolic disorders
- Neurological disorders Depression, anxiety disorder, Alzheimer's disease, Parkinson's disease, cerebral ischemia/stroke injury.
- Cardiovascular metabolic diseases Atherosclerosis, hypertension, myocardial ischemia, type 2 diabetes and its complications.
- Other Chronic fatigue syndrome, weakened immune function, and altitude sickness.

5. Evaluation of drug properties

Based on classic pharmacological criteria such as Lipinski's Rule of Five (Ro5) and our speculation on the physicochemical properties of 3-hydroxysalidrosin-4-O-glucoside, a preliminary evaluation of its potential for drug development is conducted

1. Lipinski's Five Rules Compliance Analysis：

   • Molecular weight (MW)Speculation:~478 Da, Exceed The upper limit of Ro5 is 500 Da (but not too much, many successful drugs are between 500-600 Da).
   • Lipid water partition coefficient (LogP)Speculation:<-2.0, far below The upper limit of LogP<5 for Ro5 indicates strong hydrophilicity.
   • Hydrogen bond donor (HBD)The molecule contains multiple alcohol hydroxyl groups and hydroxyl groups on the sugar ring, in terms of quantity May exceed The 5 upper limits of Ro5.
   • Hydrogen bond acceptor (HBA)There are numerous oxygen atoms on the sugar ring and glycosidic bond May exceed 10 upper limits for Ro5.
   • Conclusion: This compound Very likely to violate Multiple items in Lipinski's Five Rules (especially HBD, HBA, and LogP) are prompted Oral bioavailability may be low Ro5 is mainly suitable for predicting passive diffusion absorption, and this compound may not belong to this category.

2. Evaluation of other key pharmacological parameters：

   • Topological Polarity Surface Area (TPSA)It is speculated that drugs with TPSA>140 Å ² are difficult to pass through the blood-brain barrier. Therefore, this compound The possibility of directly penetrating BBB is very small This is an unfavorable factor for the treatment of central nervous system diseases, but can be compensated for by prodrug modification or utilizing peripheral mechanisms.
   • Solubility and permeability High water solubility and low permeability, belonging to the Biopharmaceutical Classification System (BCS)Class III (high solubility and low permeability) chemical compound. Its oral absorption may rely on active transport (such as the glucose transporter SGLT1 in the intestine mediating its absorption), but the efficiency is uncertain.
   • Metabolic stability As glycoside compounds, they are easily hydrolyzed by glycosidases in gut microbiota and intestinal epithelial cells to produce aglycones or monoglycosides, which may result in extremely low concentrations of their prototype drugs in the blood, but the metabolites may be active.
   • Toxicity warning Phenylethanoid glycosides are usually less toxic. Its structure does not contain common toxic warning groups (such as strong alkylating agents, unstable esters, etc.). But systematic in vitro and in vivo toxicology studies are needed to confirm.

3. Comprehensive potential and optimization direction of traditional Chinese medicine：

   • Preliminary assessment As a prototype of oral medication, its pharmacological properties face challenges, with the main obstacles being Poor membrane permeability and potential metabolic instability caused by excessively high polarity and molecular size。
   • Potential optimization strategies：
     • Prodrug design Esterification, acylation, or alkylation modification of excess hydroxyl or sugar groups to temporarily reduce polarity (decrease TPSA, increase LogP), improve membrane permeability and metabolic stability, and then hydrolyze back to the active form in vivo.
     • Exploration of administration routes Consider developing injection(such as intravenous injection for acute stroke or myocardial ischemia) or Mucosal drug delivery system If administered intranasal, it may bypass the BBB and enter the brain directly, avoiding the bottleneck of oral absorption.
     • As a lead compound Its unique 3-hydroxy-4-O-disaccharide structure is a valuable pharmacophore that can be used for structural simplification or modification, and to search for analogs that retain activity but have better pharmacological properties.

6. Research Status and Application Prospects

Current research status：
At present, there is extremely limited public research literature on 3-hydroxysalidrosin-4-O-glucoside. It is mainly mentioned as a chromatographic peak or mass spectrometry characteristic ion in the chemical fingerprint of Rhodiola rosea plants, and its separation and purification, structural confirmation, and systematic biological function screening work still need to be further carried out. This puts it in the realm of natural product research Early detection stage The known information mainly comes from the natural product compound library (such as product number BP2388), indicating that it has been isolated and preliminarily characterized, but deep data mining has not yet been completed.

Future research directions and prospects：
1. Deepening basic research：
- At the chemical level The primary task is to complete precise molecular structure analysis (including absolute configuration), comprehensive physical and chemical property determination, and establish efficient chemical or biosynthetic methods, providing a material basis for subsequent research.
- Pharmacological aspect: Carry out extensive In vitro activity screening Covering multiple models including antioxidant, anti-inflammatory, neuroprotective, cardiovascular protective, and metabolic regulation, to clarify its core activities. Furthermore, by utilizing techniques such as gene knockout, RNA interference, and molecular docking, we aim to explore its potential Direct target action Clarify the precise molecular mechanism.
- Pharmacokinetic study: It is crucial. It is necessary to clarify its absorption, distribution, metabolism (especially the hydrolysis process of glycosidic bonds) and excretion characteristics under different administration routes, and identify its true in vivo active form.

1. Application prospects and prospects：
   • As a functional food or health supplement additive Given the overall safety and reputation as an "adaptogen" of Rhodiola rosea, this compound is expected to be developed as a core ingredient in dietary supplements for anti fatigue, stress relief, and immune enhancement after passing safety evaluations.
   • As a lead compound for drugs Despite its limited medicinal properties, it has a novel structure and great potential for activity. Through reasonable Pharmaceutical chemical modification It is expected to develop new candidate drugs with better pharmacokinetic properties for the treatment of depression, neurodegenerative diseases, or ischemic cardiovascular and cerebrovascular diseases.
   • As a tool molecule It can be used to study the structure activity relationship (SAR) of phenylethanoid glycosides, especially the influence of glycosylation position and quantity on biological activity, target selectivity, and metabolic fate, which has important scientific value.

Conclusion：
3-Hydroxy salidrosin-4-O-glucoside is an untapped chemical entity in the treasure trove of Rhodiola rosea, a "medicinal food homology". It inherits the basic activity framework of phenylethanoid glycosides, but is also variable due to unique hydroxylation and glycosylation modifications. Currently, it is standing at the threshold of transitioning from basic research to application development. Faced with challenges in drug development, modern drug research and development technologies such as prodrug strategies and novel drug delivery systems provide multiple solutions. Future research requires close collaboration among multiple disciplines such as chemistry, pharmacology, and pharmacy to comprehensively promote target discovery, mechanism elucidation, and formulation innovation. Only then can this natural molecule originating from high mountains and polar regions be transformed into potential drugs or functional products that benefit human health, continuing the medicinal legend of Rhodiola rosea for thousands of years.