This compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.
External Descriptors
an aromatic S-hydroxynitrile
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Bewertungen
Kundenbewertungen
Application Protocols
No validated bioassay or immunoassay application protocols are provided for this small‑molecule reagent. For synthetic or analytical use, follow standard organic chemistry procedures under inert atmosphere and light protection as indicated in the Product Data. If employing biocatalysis (e.g., nitrilase or hydroxynitrile lyase), consult enzyme supplier protocols and optimize substrate loading, pH, and co‑solvent to minimize cyanohydrin dissociation and HCN release.
Biological Roles
Literature context (biochemistry; not medical/clinical):
Biosynthetic intermediate: 4‑Hydroxymandelonitrile is a central intermediate in the cyanogenic glycoside pathway in several plants (e.g., Sorghum bicolor). It arises from L‑tyrosine via p‑hydroxyphenylacetaldoxime and subsequent P450‑mediated steps, with 4‑hydroxymandelonitrile formed then rapidly glucosylated to dhurrin by UDP‑glycosyltransferases.
Enzymology: Cytochrome P450s (e.g., CYP79/CYP71 families) generate the oxime and nitrile intermediates; a dedicated glucosyltransferase converts 4‑hydroxymandelonitrile to the stable O‑glucoside. Nitrilases and hydroxynitrile lyases can further transform the aglycone, providing routes to amide/acid or back to aldehyde + HCN.
Chemical ecology: As part of cyanogenic systems, the aglycone can release HCN upon tissue damage and enzymatic activation; in planta, storage as a glycoside mitigates self‑toxicity until needed (defense mechanism). The free aglycone is typically short‑lived in biological matrices.
Physicochemical features relevant to biology: The phenolic group modulates acidity and hydrogen bonding with enzymes and transporters; the benzylic stereocenter allows enzyme‑mediated stereocontrol. The nitrile confers metabolic stability yet is a latent handle for hydrolysis or reduction by specialized enzymes.
Note: The above reflects general biochemical roles documented in the literature for 4‑hydroxymandelonitrile and related cyanohydrins and is provided for research planning. It does not constitute any claim of physiological activity for this catalog item.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare biological buffers. In aqueous solution, cyanohydrins can dissociate, and the phenolic group does not provide a practical buffering range under typical laboratory conditions. For solution‑phase work, use neutral, well‑buffered systems only when required for a transformation (e.g., biocatalysis), with stringent pH control and cyanide safety measures. For buffer selection guidance, refer instead to standard buffer systems (phosphate, HEPES, Tris, etc.).
Green Alternatives
Context: Cyanohydrins raise EHS concerns primarily due to potential HCN release. Greener choices focus on reducing cyanide hazard, solvent impacts, and energy use (literature guidance).
Cyanation alternatives
Use less hazardous cyanide sources (e.g., ferrocyanide salts, Zn(CN)2) for aryl/alkyl cyanations instead of free HCN/alkali cyanides. Tradeoff: often requires higher temperatures and transition metals; atom economy and waste profiles may worsen.
In situ cyanide generation from acetone cyanohydrin (ACH) can reduce direct handling of HCN; however, ACH carries its own hazards and regulatory constraints.
Using DL‑4‑Hydroxymandelonitrile as a “masked cyanide” synthon
Advantage: Can introduce the “CN and OH” motif without bubbling HCN; amenable to biocatalytic routes that operate in water at ambient temperature.
Drawback: Stability limits and potential HCN liberation still necessitate strict controls and closed systems.
Solvent greening (typical choices)
Prefer EtOAc, 2‑MeTHF, MeOH/EtOH over DMF/DMSO/CH2Cl2 when compatible. Acetonitrile offers a pragmatic balance of performance and safety compared to halogenated solvents.
Energy and process intensification
Enzymatic hydrolysis/hydration of the nitrile (nitrilase/nitrile hydratase) at ambient temperatures can replace harsh acid/base hydrolysis, reducing energy and neutralization salt waste.
Comparison snapshot (literature)
Route: Acidic nitrile hydrolysis vs. nitrilase-catalyzed hydration
Pros (biocatalysis): Mild, aqueous, lower salt load, enantioselective options.
Cons: Enzyme sourcing, potential substrate inhibition, need for pH control to suppress cyanohydrin dissociation.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item; refer to CoA/Spec Sheet.
Role as an intermediate: DL‑4‑Hydroxymandelonitrile serves as a functionalized aryl building block in small‑molecule process routes where the nitrile can be transformed to carboxamides/acids or reduced to primary amines, and the benzylic alcohol enables further diversification (esterification, carbonate formation, oxidation to ketone/aldehyde equivalents under controlled conditions).
Chiral considerations: When single‑enantiomer products are needed, enzymatic resolution or asymmetric cyanation of 4‑hydroxybenzaldehyde (e.g., using hydroxynitrile lyases) can deliver enantioenriched intermediates for downstream API synthesis.
Formulation relevance: The compound itself is reactive and not suited as a formulation excipient. If present in a process, containment strategies must address potential HCN release, with appropriate quench and scrub solutions validated at scale.
Regulatory and handling note
Cyanide‑releasing intermediates may trigger additional process safety, waste handling, and worker exposure controls in GMP environments. Engage EHS and QA early to align on monitoring (e.g., cyanide in air, waste streams) and specification setting (residual cyanide, aldehyde content), where applicable.
Physical Properties
Item-specific specifications (this lot)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/estimated physicochemical data (for reference only; not product specifications)
Molecular formula: C8H7NO2 (literature)
Molecular weight: ~149.15 g/mol (literature)
Acid–base: Phenolic pKa typically ~9–10 in water for para‑substituted phenols; benzylic alcohol pKa much higher (literature).
LogP: Expected moderate polarity due to phenol and alcohol; nitrile adds polarity; reported logP for analogous p‑substituted mandelonitriles is around 1–2 (literature, varies with ionization and solvent).
Solubility: Generally soluble in polar protic and aprotic organic solvents (MeOH, EtOH, acetone, acetonitrile, DMSO). Limited stability in aqueous media due to cyanohydrin dissociation (literature). Water solubility is moderate but practical use in water is discouraged unless pH is carefully controlled (literature).
Boiling point: Not typically applicable; compound likely decomposes before boiling (literature expectation for cyanohydrins).
Melting point: Reported values for related p‑hydroxy cyanohydrins span ca. 80–120 °C depending on purity and solvation; specific MP for this item is not established here (literature range only).
Density/Refractive index/UV cutoff/Residue on ignition/Metal content: Not specified for this item; refer to CoA/Spec Sheet.
Practical note (literature)
Cyanohydrins can rearrange or dissociate under heat, acid, or base; handle at ambient or lower temperatures and minimize exposure to moisture to preserve integrity.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance)
For synthetic building blocks like DL‑4‑Hydroxymandelonitrile, “Analytical Reagent (AR)” or “Purified” grades typically specify limits on common impurities (water, inorganic salts, residual solvents) and may define chromatographic purity by GC/HPLC. “HPLC grade” refers to low UV-absorbing backgrounds and stringent particulate limits suitable for chromatography but is less relevant for a reactive cyanohydrin.
If a stabilizer is present (e.g., trace base/acid scavengers or antioxidants), it can influence reactivity in acid/base‑catalyzed or metal‑mediated transformations. Absence/presence of stabilizers should be verified on the CoA before use in sensitive reactions.
Recommendations for users
Verify enantiomeric composition: This listing is DL (racemate). If an enantioenriched cyanohydrin is required (e.g., for asymmetric synthesis or chiral resolution), confirm ee on the CoA or procure enantioenriched material.
Confirm residual water and free cyanide levels when critical: Cyanohydrins are moisture sensitive; Karl Fischer water and cyanide content may be reported on request. If not reported, perform in‑house checks prior to moisture‑sensitive steps.
For spectroscopic or kinetic studies, request/confirm UV–Vis background and trace metal content where relevant. Otherwise: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
DL‑4‑Hydroxymandelonitrile is a versatile α‑hydroxynitrile (cyanohydrin) used as a benzylic, para‑hydroxy‑substituted building block. Key application families (literature):
Precursor to acids/amides: Hydrolysis of the nitrile (acidic or basic) affords 4‑hydroxymandelic acid or the corresponding amide via stepwise hydration. Typical conditions employ mineral acids (H2SO4, HCl) or base (NaOH) with aqueous organic solvents and heat.
Reductive transformations: Catalytic hydrogenation (Raney Ni, Pd/C) or hydride reagents (LiAlH4, BH3·THF) convert the nitrile to primary amines, giving para‑hydroxy‑2‑amino‑1‑phenylethanol derivatives. Control of chemoselectivity (nitrile vs aryl/benzylic functions) requires appropriate catalyst and solvent.
Protective group chemistry: The phenolic OH can be protected (TBS, TBDMS, benzyl) to increase compatibility with strong bases/nucleophiles; the secondary alcohol can be esterified or converted to a carbonate, enabling later unmasking of the cyanohydrin motif.
Enzymatic routes: Oxynitrilases and nitrilases/nitrile hydratases enable enantioselective formation or downstream hydrolysis, allowing access to single‑enantiomer 4‑hydroxymandelic derivatives.
Access to cyanogenic glycoside motifs: Serves as the aglycone intermediate en route to dhurrin analogs (via O‑glycosylation of the phenol), valuable in plant natural product studies.
Disconnection strategy: Functions as a masked 4‑hydroxybenzaldehyde + “CN” synthon. Under controlled (mildly basic or Lewis acid) conditions, reversible release of the aldehyde can be exploited for in situ generation and capture in aldol or imine chemistry, minimizing direct HCN handling.
Practical tips
Maintain neutral, anhydrous conditions during setup to minimize decomposition. Protect from light and use inert atmosphere as provided in Product Data. Adjust pH only immediately before intended transformation.
Reaction Conditions
General conditions from literature (guidance only; optimize per substrate and scale):
Nitrile hydrolysis → amide/acid
Acidic: 3–6 M HCl or H2SO4 in aqueous MeOH/MeCN, 50–90 °C, 2–16 h; amide observed at shorter times/lower water activity; complete to acid with longer time/heat. Work under closed systems; neutralize cyanide traces in waste.
Basic: 2–5 M NaOH/KOH in aqueous EtOH/H2O, 40–80 °C, 2–12 h; may cause cyanohydrin cleavage. Protect phenol if O‑acylation/alkylation by base is undesirable.
Nitrile reduction → primary amine
Catalytic hydrogenation: 5–10 wt% Pd/C or Raney Ni, 1–10 bar H2, EtOH/MeOH/EtOAc, 20–60 °C, 2–8 h. Add acid scavenger carefully; monitor to prevent over‑reduction.
Hydride reduction: LiAlH4 (THF, 0–25 °C), then quench at low temperature; or BH3·THF (0–25 °C). Protect phenol to avoid side reactions; exclude moisture stringently.
Benzylic oxidation (secondary alcohol → carbonyl)
Dess–Martin periodinane, CH2Cl2 or MeCN, 0–25 °C, 0.5–2 h; or TEMPO/bleach variants in biphasic systems with careful pH control to avoid cyanohydrin cleavage.
Phenol protection
TBSCl, imidazole, DMF, 0–25 °C; or BnBr, K2CO3, acetone/MeCN, reflux. Confirm that base does not induce significant cyanohydrin loss.
Enzymatic steps
Nitrilase: pH 7–8, 20–35 °C, aqueous buffer with 5–30% co‑solvent (MeCN/EtOH), hours to overnight; affords acid with minimal salts.
Monitoring and analysis
Use HPLC with UV at 220–280 nm; consider derivatizing the aldehyde or cyanide if equilibrium complicates quantitation. Maintain inert, dry conditions where feasible.
Safety and Handling
Item-specific hazard statements
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to the product SDS for authoritative safety information.
General safety guidance for cyanohydrins (literature; not a substitute for SDS)
Key hazards: Cyanohydrins may liberate hydrogen cyanide (HCN), especially under acidic or basic conditions, on heating, or upon prolonged contact with moisture. HCN is acutely toxic by inhalation, ingestion, and skin absorption.
Likely hazard classes: Acute toxicity (oral/dermal/inhalation), specific target organ toxicity, and aquatic toxicity are commonly associated with cyanide-releasing substances (literature patterns). Phenolic functionality may confer skin/eye irritation potential.
PPE: Use chemical-resistant gloves (e.g., butyl rubber or laminated barrier for cyanide risk), lab coat, splash goggles/face shield. Employ a fume hood for all handling, transfers, and weighing.
Incompatibilities: Strong acids/bases (promote cyanohydrin dissociation to HCN and 4‑hydroxybenzaldehyde), strong oxidizers, and strong nucleophiles. Avoid prolonged contact with water; moisture and elevated temperature accelerate decomposition.
First aid (overview; follow SDS/site SOPs): Move to fresh air if inhaled; rinse skin/eyes with water for ≥15 minutes if contacted; do not induce vomiting if ingested; seek immediate medical attention for suspected cyanide exposure. Facilities handling cyanide-releasing materials should have cyanide emergency response procedures in place.
Engineering controls: Work in a certified chemical fume hood; keep containers tightly closed under inert gas. Use secondary containment and cyanide‑compatible spill kits.
Storage: As provided in Product Data—store under argon, protected from light, at room temperature; keep dry.
Solvent Selection
Given the bifunctional nature (phenol + secondary alcohol + nitrile), DL‑4‑Hydroxymandelonitrile is best handled in polar organic solvents while minimizing water to suppress cyanohydrin dissociation.
Moderately soluble: Dichloromethane, THF (watch for basic stabilizers in THF), 2‑MeTHF.
Limited: Alkanes, toluene, hexanes (unless warmed or with cosolvent).
Aqueous systems: Use sparingly; pH control is essential to suppress HCN release and decomposition.
Selection guidance
Reaction media: For nitrile hydrolysis, use aqueous alcohols or polar aprotics with controlled acid/base. For reductions (e.g., catalytic hydrogenation), EtOH/MeOH or EtOAc with suitable catalysts is common. For enzymatic transformations (oxynitrilase/resolution), buffered aqueous–organic mixtures at controlled pH (≥10 for phenolate or ~5–7 to suppress dissociation) are used.
Workup/crystallization: Ethyl acetate/hexanes or toluene/EtOAc mixtures can help isolate product while limiting prolonged contact with water. For sensitive manipulations, strictly anhydrous acetonitrile or acetone under inert gas is advantageous.
Small comparison (literature)
MeOH/EtOH: Excellent solubility, convenient for hydrogenation/hydrogenolysis; may accelerate cyanohydrin equilibration under acid/base.
Acetonitrile: Good for neutral/oxidative conditions; minimal proticity helps stability.
DMSO/DMF: High solubility; challenging removal; avoid strong base to prevent decomposition.
Aqueous buffers: Enable biocatalysis but demand strict pH control to limit HCN release.
Storage and Reconstitution
Item-specific (Product Data)
Storage conditions: Protected from light; Room temperature; Argon charged.
Shipping: Normal.
Best practices (literature/good lab practice)
Containerization: Store in amber, tightly sealed containers with headspace flushed with inert gas (argon or nitrogen). Include desiccant when possible to limit moisture ingress. Avoid ground‑glass joints that can seize; use PTFE‑lined caps.
Stability considerations: Cyanohydrins can slowly equilibrate to aldehyde + HCN, accelerated by moisture, acids, bases, and heat. Maintain neutral, dry conditions. Avoid repeated temperature cycling.
In‑use handling: Open only in a fume hood. Minimize time open to air. If weighing small portions, consider pre‑aliquoting under inert atmosphere.
Solution preparation: Prepare solutions immediately before use. Favor anhydrous solvents (MeCN, acetone, EtOAc, alcohols dried) under inert gas. In aqueous or mixed media (for biocatalysis), strictly control pH and temperature; use closed vessels and appropriate cyanide scrubbing for off‑gas.
Shelf life: Not specified for this item; refer to CoA/Spec Sheet. Monitor by HPLC/GC or 1H NMR for signs of decomposition (appearance of 4‑hydroxybenzaldehyde or free cyanide).
Disposal: Treat residues and rinses as cyanide‑bearing waste. Follow institutional and regulatory procedures for cyanide neutralization and disposal; never acidify cyanide wastes.
Structure and Identity
DL-4-Hydroxymandelonitrile is the racemic cyanohydrin of 4‑hydroxybenzaldehyde, bearing a benzylic secondary alcohol adjacent to a nitrile and a para-phenolic substituent on the aryl ring.
Item-specific (Product Data)
SKU: S160988
CAS: 13093-65-7
InChIKey: 126993 (as provided)
Storage conditions: Protected from light; Room temperature; Argon charged
Shipped in: Normal
Research use: For research use only
Literature/computed identifiers and features (for reference; not item specifications)
2D structural description: A benzene ring bearing a para‑OH; at the benzylic carbon is a secondary alcohol [–CH(OH)–] that also carries a nitrile (–C≡N). The benzylic stereocenter is racemic (DL).
Structural features relevant to reactivity: The α‑hydroxynitrile motif is prone to reversible cyanohydrin dissociation to 4‑hydroxybenzaldehyde + HCN under acidic/basic catalysis; phenolic OH imparts additional hydrogen bonding and acidity.
General notes
Being a cyanohydrin, it exists in equilibrium with its parent aldehyde and hydrogen cyanide in the presence of acid/base catalysts or water, with equilibrium position influenced by pH, solvent, and temperature (literature).
Synthetic Utility
Functional group portfolio and reactivity (literature):
α‑Hydroxynitrile motif
Hydrolysis: Nitrile → amide/acid (controlled hydration/hydrolysis) to access 4‑hydroxymandelamide or 4‑hydroxymandelic acid.
Reduction: Nitrile → primary amine, yielding p‑hydroxy‑2‑amino‑1‑phenylethanol scaffolds (precursors to β‑amino alcohols, ligands, and fine chemicals).
Equilibrium cleavage: Under acid/base catalysis, reversible formation of 4‑hydroxybenzaldehyde + HCN; can be exploited for in situ aldehyde delivery while minimizing direct HCN handling.
Phenolic handle
Protection: TBS, TBDMS, MOM, benzyl protections expand compatibility with strong nucleophiles/bases and enable orthogonal deprotection.
O‑Alkylation/Acylation: Access para‑alkoxy or para‑acyloxy derivatives to tune solubility and electronic properties for subsequent steps.
Benzylic secondary alcohol
Oxidation: Selective oxidation (e.g., Dess–Martin, TEMPO) to the corresponding α‑keto nitrile (mandelonitrile → benzoyl cyanide analogs) can be achieved under carefully anhydrous, neutral conditions.
Derivatization: Conversion to esters/carbonates/halides to serve as leaving groups in substitution or to generate nitrile‑stabilized carbocations for C–C bond formation.
Retrosynthetic value
Serves as a convergent junction of 4‑hydroxybenzaldehyde and a cyanide equivalent; enables late‑stage introduction of nitrile/acid/amine functionality without early exposure to harsh cyanation conditions.
Practical advice
Keep operations neutral/dry; protect phenol when needed. Monitor by HPLC/GC with derivatization if necessary, as cyanohydrin/aldehyde equilibria can complicate direct analysis.
Target Specificity
Not applicable. This catalog item is a small‑molecule reagent, not a biological targeting agent. No antigen/epitope, clone, isotype, or species reactivity information applies. Item‑specific targeting details are not provided for this product.
Wir verwenden Cookies, um die ordnungsgemäße Funktion der Website sicherzustellen und, soweit zulässig, Ihr Nutzererlebnis zu verbessern. Sie können Ihre Einstellungen jederzeit unter „Einstellungen“ verwalten. Weitere Informationen finden Sie in unserer Cookie-Richtlinie.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
G2616623