Prostaglandin B2-d , CAS No.211105-23-6

CAS: 211105-23-6 Cat. No.: P1450745 PubChem CID: 91872427

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Prostaglandin B2-d 4 is the deuterium labeled Prostaglandin B2.

Specifications

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CCCCCC(C=CC1=C(C(=O)CC1)CC=CCCCC(=O)O)O
• IUPAC Name: (Z)-3,3,4,4-tetradeuterio-7-[2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopenten-1-yl]hept-5-enoic acid
• InChIKey: PRFXRIUZNKLRHM-GKNRUGNGSA-N
• INCHI: 1S/C20H30O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h4,7,12,14,17,21H,2-3,5-6,8-11,13,15H2,1H3,(H,23,24)/b7-4-,14-12+/t17-/m0/s1/i5D2,8D2
• PubChem CID: 91872427

Application Protocols

No item‑specific, tested application protocols were provided. General guidance for analytical use (literature, best practice):

• Preparation of stock solutions

• Warm solvent (EtOH, ACN, or DMSO) to room temperature; purge vial with N2/Ar; quickly weigh compound in amber glass; dissolve to 0.5–10 mg/mL. Vortex gently; avoid sonication heating.
• Aliquot into low‑bind, amber vials; blanket with inert gas; store at −20°C or colder.

• LC‑MS/MS method development

• Start with C18 column; gradient 30→95% ACN with 0.05% formic or acetic acid over 10–15 min; ESI− preferred for carboxylates. Optimize source temperature and declustering potential for labeled/unlabeled species.
• Use isotope‑dilution where applicable; construct calibration curves across expected concentration range with matched matrix.

• QC and stability

• Assess short‑term stability by replicate injections over 24–48 h at autosampler temperature; evaluate carryover and adsorption by recovery tests from glass vs. plastic.

These are general recommendations; adjust to your instrumentation and regulatory requirements.

Biological Roles

Literature, general context for prostaglandin B2 (PGB2):

• Origin and biogenesis

• PGB2 is commonly described as a non‑enzymatic dehydration product of PGE2, forming under acidic or thermal conditions and during sample handling. It is part of the broader eicosanoid network derived from arachidonic acid via the cyclooxygenase pathway.

• Functional considerations

• Unlike primary prostanoid mediators (PGE2, PGD2, PGF2α, PGI2, TXA2), B‑series prostaglandins are generally considered downstream/isomerization products with reduced canonical receptor activity; they may, however, serve as markers of sample handling artifacts and oxidative stress in analytical studies.

• Research implications

• Inclusion of PGB2 standards in lipidomics panels assists in distinguishing genuine biosynthetic products from ex vivo dehydration artifacts.
• Deuterated analogs are particularly valuable for isotope‑dilution quantification, enabling correction of matrix effects and recovery.

No medical or clinical claims are made. This product is intended strictly for research use, such as method development, calibration, and metabolic pathway investigations.

Buffer Applications

This compound is a hydrophobic lipid standard and is not typically used to formulate aqueous buffer systems. Practical notes:

• If aqueous work is required, prepare a concentrated stock in DMSO or ethanol and dilute into buffer immediately before use, often with carrier protein (e.g., 0.1% fatty‑acid‑free BSA) or non‑ionic surfactant to aid dispersion. • Avoid strongly basic or acidic buffers that can accelerate enone isomerization/decomposition. Work cold, protect from light, and minimize exposure time in aqueous media.

For buffer selection and pH control, focus on method requirements for your assay rather than this compound serving as a buffering agent.

Green Alternatives

While this item is a specialized lipid standard rather than a bulk solvent or reagent, greener handling choices can reduce environmental and safety burdens.

• Prefer greener solvents for solution preparation (literature, general)

• Favor ethanol or acetonitrile (low toxicity, readily recoverable) over chlorinated solvents like dichloromethane or chloroform when solubility and method compatibility permit.
• Avoid ether solvents that can form peroxides during long storage unless necessary; if used, test for peroxides.

• Minimizing waste and exposure

• Prepare concentrated stock solutions and dilute at point‑of‑use to reduce solvent volumes.
• Use micro‑aliquoting to prevent repeated thawing and disposal of aged solutions.
• Implement closed autosampler vials and low‑dead‑volume fittings to minimize evaporative losses and emissions.

• Comparison (general)

• Ethanol vs. DCM: EtOH is renewable and less hazardous; DCM offers broader solubility but higher toxicity and environmental impact.
• Acetonitrile vs. THF: ACN has favorable MS baseline and is less prone to peroxide formation; THF offers strong solvation but is peroxide‑forming and often requires stabilizers.

• Packaging/handling

• Select amber glass vials with PTFE‑lined caps (reusable/recyclable) and minimize plastic disposables where possible.

Pharmaceutical Uses

No excipient or pharmacopeial status is specified for this item. This material is supplied for research use only.

• Typical roles in pharmaceutical R&D (literature, general)

• Reference standard or system suitability control in analytical methods (e.g., LC‑MS) evaluating prostaglandin content, degradation, or impurity profiles in drug substances/formulations.
• Tool compound for metabolism/stability studies to understand dehydration/isomerization pathways of prostanoids during processing and storage.

• Quality considerations

• For regulated workflows, ensure traceable calibration, verified purity, and (if deuterated) certified isotopic enrichment. Maintain documentation (CoA, SDS) and implement appropriate storage and handling controls (light/oxygen protection).

No therapeutic or clinical claims are made or implied.

Physical Properties

Item-specific physicochemical specifications were not provided. The following are general/literature characteristics for prostaglandin B2–type compounds; values can vary with isotopic labeling and salt/ester form.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet. • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet. • Melting point / boiling point: Not typically reported for labile lipid standards; prostaglandins are amorphous/oily and decompose before boiling (literature, general). • Density/refractive index: Not commonly specified for these analytes (literature, general). • Solubility (literature, general):

• Readily soluble in polar aprotic organic solvents (e.g., acetonitrile, DMSO), lower alcohols (methanol, ethanol), and chlorinated solvents (DCM, chloroform).
• Sparingly soluble in water at neutral pH due to predominately lipophilic skeleton; solubility increases in basic aqueous media via carboxylate formation. • LogP/logD (literature, general): Moderate-to-high lipophilicity expected for prostanoids; exact value depends on ionization state and labeling. • pKa (literature, general): Carboxylic acid typically pKa ~4–5 for prostanoids; exact value for this item not specified. • Stability (literature, general): Sensitive to light, oxygen, and base/acid-catalyzed isomerization; store frozen, minimize exposure to elevated temperature.

Always consult the item’s CoA/Spec Sheet for definitive specifications.

Quality & Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting grade for lipid standards (general guidance)

• High‑purity prostaglandin standards are typically supplied at ≥95–98% purity by HPLC/UPLC, with isomeric impurities (e.g., A/B/E series interconversions) reported on the CoA. Low‑level peroxide/aldehyde content from autoxidation may be monitored.
• For deuterated materials (“-d”), the isotopic enrichment and labeling pattern (e.g., d4, d5, d9) are critical for quantitative LC‑MS; these parameters should be explicitly stated on the CoA. In the absence of such data here, confirm with the batch documentation.

• Implications for use

• Analytical calibration: Verify purity and isotopic pattern to correctly prepare gravimetric standards and to avoid bias in isotope‑dilution assays.
• Chromatographic background: High‑grade solvents and low‑UV chromophores reduce baseline noise; verify that the grade supports your detection mode (UV, MS, or electrochemical).

• Documentation

• Request and review the lot‑specific CoA for: purity assay method and result, residual solvent profile, water content (if relevant), isotopic enrichment (if deuterated), and recommended handling/storage conditions.

Reaction & Applications

This product is primarily a research/analytical lipid standard rather than a reagent for stoichiometric synthesis. Relevant applications (literature, general):

• Analytical/lipidomics

• Use as a reference compound or internal standard in LC‑MS/MS workflows profiling prostaglandins/prostanoid dehydration products. Deuterated analogs (“-d”) are commonly employed for isotope‑dilution quantitation; confirm isotopic enrichment on the CoA.
• Employed to evaluate non‑enzymatic dehydration of PGE‑series prostaglandins and to study stability/isomerization during sample preparation.

• Chemical reactivity/derivatization

• Carboxylic acid can be esterified (e.g., methyl or pentafluorobenzyl esters) to enhance GC‑MS volatility/sensitivity; typical coupling via diazomethane (caution) or carbodiimide/DMAP methods (literature).
• Hydroxy functions (if present in the specific structure) can be silylated (TMS/TBDMS) to stabilize and improve chromatographic behavior.
• Conjugated enone system is prone to Michael additions and isomerization under basic/acidic conditions—control pH and temperature to preserve native structure.

• Practical notes

• Perform derivatizations under anhydrous, oxygen‑limited, low‑light conditions. Verify product identity by high‑resolution MS and diagnostic UV (conjugated diene/enone absorbance) where applicable.
• For calibration solutions, prepare gravimetrically using LC‑MS grade solvents; validate concentration by quantitative NMR or UV if appropriate.

Reaction Conditions

Typical conditions relevant to derivatization and analysis of prostaglandin standards (literature, general; verify for your method):

• Esterification

• Diazomethane (CH2N2) in ether, 0–5°C, seconds to minutes, gives methyl esters quantitatively; handle with extreme caution due to toxicity/explosivity.
• Carbodiimide coupling (e.g., EDC•HCl, DMAP, MeOH), 0–25°C, 0.5–2 h, affords alkyl esters without harsh conditions.
• Pentafluorobenzyl esters: PFBBr, DIPEA, ACN or DMF, 0–25°C, 0.5–2 h; enhances GC‑MS (NCI) sensitivity.

• Silylation of hydroxy groups (if present)

• BSTFA + 1% TMCS, acetonitrile or pyridine, 60–70°C, 15–30 min; yields TMS ethers for GC‑MS.

• LC‑MS analysis (underivatized)

• Mobile phase: water/acetonitrile with 0.01–0.1% acetic or formic acid; column temperature 30–40°C; monitor multiple reaction monitoring (MRM) transitions appropriate to the isotopic label.
• Protect from light; autosampler at 4–8°C; analyze within 24–48 h for best stability.

• Stability controls

• Include antioxidant (e.g., 0.01% BHT) only if compatible with detection; use amber vials and inert atmosphere. Avoid prolonged exposure to pH >8 or <3 to limit isomerization/degradation.

Note: Conditions vary with instrument and derivatization strategy; optimize empirically and consult primary literature.

Safety & Handling

• GHS classification and hazard statements: Not specified for this item; refer to SDS. • Signal word/pictograms: Not specified for this item; refer to SDS.

• General safety guidance for prostaglandin standards (literature/best practice)

• Handle in a chemical fume hood; avoid inhalation, ingestion, and skin contact. Prostaglandins and analogs can be biologically active at very low concentrations; practice stringent contamination control.
• Wear appropriate PPE: lab coat, nitrile gloves (double‑glove for extended handling), and splash goggles. Change gloves frequently when handling organic solutions.
• Avoid sources of oxidation and strong light; use amber glassware and inert gas (N2/Ar) blanket for solution handling.

• Incompatibilities (general)

• Strong bases and strong acids (can induce isomerization/decomposition of the conjugated enone system and hydrolysis of esters if present).
• Oxidizing agents; prolonged exposure to air/oxygen promotes peroxidation of unsaturated chains.

• First aid (overview; defer to SDS)

• Skin/eye contact: Rinse with copious water for ≥15 minutes; remove contaminated clothing; seek medical advice.
• Inhalation: Move to fresh air; monitor breathing; obtain medical attention if symptoms occur.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Spill/cleanup

• Absorb small spills with inert material; collect in sealed containers for disposal. Avoid aerosolization; decontaminate surfaces with solvent followed by detergent.

Always consult the product SDS for authoritative safety information.

Solvent Selection

• Polarity and miscibility (literature, general for prostaglandins)

• Amphiphilic weak acids with substantial hydrophobic character; practically insoluble in water at neutral pH but soluble in MeOH, EtOH, isopropanol, acetonitrile, DMSO, THF, ethyl acetate, and chlorinated solvents.
• Water solubility increases in basic aqueous media (carboxylate form), but base can catalyze isomerization—use minimal base and keep cold.

• Recommended handling solvents

• Stock solutions: ethanol, methanol, acetonitrile, or DMSO (LC‑MS grade). For bioassays, DMSO or ethanol stocks diluted into buffered media containing carrier proteins (e.g., 0.1% fatty‑acid‑free BSA) can improve delivery; validate for your system.
• Avoid prolonged exposure in highly basic/acidic media and avoid oxidizing chlorinated solvents unless strictly necessary.

• When to choose alternatives

• For maximum stability and MS cleanliness: acetonitrile or ethanol over chlorinated solvents.
• For aqueous workup: use co‑solvent systems (e.g., 10–50% ACN or EtOH in buffer) and minimize pH extremes.

• Practical tips

• Use amber vials, pre‑cooled solvents, and inert gas blankets. Prepare small aliquots to limit freeze‑thaw cycles.
• If adsorption losses are observed, pre‑rinse plastics with solvent or use silanized glassware.

Storage & Reconstitution

• Item-specific storage and shipping (from Product Data)

• Storage Conditions: Store at −20°C.
• Shipped In: Ice chest + Ice pads.

• General best practices for prostaglandin standards

• Protect from light and oxygen. Keep tightly sealed in amber glass vials with PTFE‑lined caps. Purge headspace with nitrogen or argon after each use.
• Store desiccated to avoid moisture ingress. For long‑term storage, consider −80°C to minimize isomerization/oxidation.

• Reconstitution and working solutions

• Use LC‑MS grade ethanol, acetonitrile, methanol, or DMSO. Typical stock concentrations: 0.5–10 mg/mL (adjust to your assay). Mix gently to dissolve; avoid elevated temperatures.
• Prepare small aliquots to minimize freeze–thaw; discard aliquots showing discoloration or unexpected LC‑MS/UV profiles.
• For aqueous applications, dilute the organic stock immediately before use; consider adding carrier (e.g., 0.1% fatty‑acid‑free BSA) if adsorption losses are problematic.

• Stability notes

• Working solutions are best used the day of preparation. If storage is necessary, keep at ≤−20°C, protected from light, and validate stability by analytical testing.

• Documentation

• For exact stability limits, concentration, and any stabilizers present, consult the lot‑specific CoA/Spec Sheet.

• Research Use Note

• For research use only.

Structure & Identity

• Item-specific identifiers (from Product Data)

• CAS: 211105-23-6
• CID: 91872427
• InChIKey: 284999 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Nomenclature and context

• Name: Prostaglandin B2-d (commonly denotes a Prostaglandin B2 analog; the “-d” suffix is often used for deuterated standards, though the isotope content and labeling positions are not specified here.)

• Structural features (general prostaglandin B-family characteristics; literature)

• 20‑carbon eicosanoid framework derived from arachidonic acid.
• Five‑membered cyclopentane/cyclopentene core with two aliphatic side chains (C-8 and C‑12 substituents in the prostanoid numbering system).
• B‑series prostaglandins arise via non‑enzymatic dehydration of E‑series prostaglandins and feature a conjugated enone/dienone system within the prostanoid core/side chain.
• Series “2” denotes two double bonds in the eicosanoid skeleton (relative to arachidonic acid origin); exact double‑bond geometry and positions should be confirmed from the CoA/SDS for this specific item.

• 2D structural description (general; literature)

• A substituted cyclopentene ring bearing: (i) an α,β‑unsaturated carbonyl motif and (ii) two pendant aliphatic chains of differing length/unsaturation, terminating in a carboxylic acid on one chain. Stereocenters typical of prostanoids are present, but absolute configuration for this item is not specified here.

Synthetic Utility

As a structurally defined prostaglandin standard, this compound is not a common building block for multistep synthesis. However, several chemical features enable selective transformations useful for analytical derivatization and structure confirmation (literature, general):

• Functional groups and reactivity

• Carboxylic acid: amenable to esterification (Me, Et, PFB) to adjust volatility and MS response.
• Conjugated enone/diene motif: UV‑active; can undergo Michael addition or isomerization—handled under neutral, oxygen‑limited conditions.
• Allylic/secondary alcohols (if present in the specific isomer): silylation (TMS/TBDMS) or acylation to modulate polarity.

• Typical transformations

• GC‑MS: Convert to methyl ester + TMS ether(s) using TMS‑Cl or BSTFA in pyridine; or PFB ester formation with PFBBr/DIPEA for negative‑ion detection.
• LC‑MS: Often analyzed underivatized; stabilization can include mild antioxidants and low‑temperature autosampler conditions.

• Retrosynthetic value

• Limited; complex stereochemistry and sensitive enone make it impractical as a generic synthon. Its main value lies in serving as an authentic standard for method development and quantitation.

Target Specificity

Not applicable. This product is a small‑molecule prostaglandin standard, not an antibody, probe, or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.