ROSIN

beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl

Molecular Formula: C15H20O6
Molecular Weight: 296.31
IUPAC name: (2E)-3-Phenylprop-2-en-1-yl β-D-glucopyranoside
Preferred IUPAC name: (2R,3S,4S,5R,6R)-2-(Hydroxymethyl)-6-{[(2E)-3-phenylprop-2-en-1-yl]oxy}oxane-3,4,5-triol
CAS Number:85026-55-7
ChemSpider: 4444255
EC Number:232-475-7
KEGG: C04183
PubChem CID:5280656
CompTox Dashboard (EPA)    :DTXSID60904535

Rosin is used on bows of violins and other stringed instruments, on the shoes of dancers, and on floors of studios and stages to prevent slipping.
Rosin is a form of concentrate — also commonly referred to as dabs — made by applying heat and pressure to cannabis plants, and more specifically, the trichomes. 
Trichomes are the oblong “crystals” coating cannabis. They also happen to be where the active ingredients in the plant are located, called cannabinoids. 
Manufacturers place bud in a special rosin bag or between two sheets of parchment paper, which is then set inside a hydraulic press outfitted with heating elements. 
Rosin is an abundantly available natural product. Rosin is a mixture of acidic (ca. 90%) and neutral (ca. 10%) compounds. 
The characteristic fused ring structure of rosin acids is analogous to that of some aromatic compounds in rigidity, and makes rosin and beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl's derivatives potential substitutes for those aromatic compounds in polymers. 
In this study, the synthesis of biobased epoxy and curing agent using rosin and the cure reaction were investigated. Abietyl glycidyl ether and methyl maleopimarate were synthesized from one of the rosin acids. 
Abietyl glycidyl ether was used as a model compound representing rosin-based epoxies, while methyl maleopimarate was used as a model compound representing rosin-based anhydride curing agents. 
The synthesis methods of the model compounds were examined and the chemical structures were confirmed by 1H NMR, 13C NMR, FT-IR and ESI-MS. 
Curing of abietyl glycidyl ether with aniline and curing of methyl maleopimarate with phenyl glycidyl ether were investigated separately. 
Nonisothermal curing of the model systems was studied by DSC, and the cured products were characterized by 1H NMR.

What is Rosin?
Rosin is a nonvolatile component of crude gum which is included largely in plants belonging to pine family (Pinaceae). 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl mainly consists of a various isomer technically called resin acids.
yellow resin (= sticky substance produced by certain trees and plants) that has become hard, used especially on the hairs of bows of stringed musical instruments to prevent the hairs from sliding over the strings
rosin, also called colophony, or colophonium, translucent, brittle, friable resin used for varnish and in manufacturing many products. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl becomes sticky when warm and has a faint pinelike odour. Gum rosin consists of the residue obtained upon distillation of the oleoresin (a natural fluid) from pine trees (the volatile component is spirit of turpentine); wood rosin, obtained by solvent extraction of the stumps, is usually of a darker colour.
Rosin and rosins chemical derivatives are used chiefly to make soaps, varnishes, sealing wax, printing inks, driers, sizes for paper, adhesives, binders, soldering fluxes, gloss oils for paints, and pitch for casks. 

Uses
Structure of abietic acid, a component of rosin
Rosin is an ingredient in printing inks, photocopying and laser printing paper, varnishes, adhesives (glues), soap, paper sizing, soda, soldering fluxes, and sealing wax.
Rosin can be used as a glazing agent in medicines and chewing gum. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is denoted by E number E915.
A related glycerol ester (E445) can be used as an emulsifier in soft drinks. In pharmaceuticals, rosin forms an ingredient in several plasters and ointments.
In industry, rosin is a flux used in soldering. 
The lead-tin solder commonly used in electronics has 1 to 2% rosin by weight as a flux core, helping the molten metal flow and making a better connection by reducing the refractory solid oxide layer formed at the surface back to metal. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenylis frequently seen as a burnt or clear residue around new soldering.
A mixture of pitch and rosin is used to make a surface against which glass is polished when making optical components such as lenses.
Rosin is added in small quantities to traditional linseed oil/sand gap fillers ("mastic"), used in building work.
When mixed with waxes and oils, rosin is the main ingredient of mystic smoke, a gum which, when rubbed and suddenly stretched, appears to produce puffs of smoke from the fingertips.
Rosin is extensively used for rosin's friction-increasing capacity in several fields:

Players of bowed string instruments rub cakes or blocks of rosin on their bow hair so Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl can grip the strings and make them "speak", or vibrate clearly.
Extra substances such as beeswax, gold, silver, tin, or meteoric iron[8] are sometimes added to the rosin to modify Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl's stiction/friction properties and the tone it produces.
Powdered rosin can be applied to new hair, for example with a felt pad or cloth, to reduce the time taken in getting sufficient rosin onto the hair. 
Rosin is often reapplied immediately before playing the instrument.
Lighter rosin is generally preferred for violins and violas, and in high-humidity climates, while darker rosins are preferred for cellos, and for players in cool, dry areas. 
There are also specific, distinguishing types for basses—for more see Bow (music).
Violin rosin can be applied to the bridges in other musical instruments, such as the banjo and banjolele, in order to prevent the bridge from moving during vigorous playing.
Ballet, flamenco, and Irish dancers are known to rub the tips and heels of their shoes in powdered rosin to reduce slippage on clean wooden dance floors or competition/performance stages. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl was at one time used in the same way in fencing and is still used as such by boxers.
Gymnasts and team handball players use Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl to improve grip. 
Rock climbers have used Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl in some locations.
Olympic weightlifters rub the soles of their weightlifting boots in rosin to improve traction on the platform.
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is applied onto the starting line of drag racing courses used to improve traction.
Bull riders rub rosin on their rope and glove for additional grip.
Baseball pitchers and ten-pin bowlers may use a small cloth bag of powdered rosin for better ball control. 
Baseball players sometimes combine rosin with sunscreen, creating a very sticky substance that allows far more grip on the ball than the rosin alone will; the use of such a substance is a violation of Major League Baseball rules.
Rosin can be applied to the hands in aerial acrobatics such as aerial silks and pole dancing to increase grip.

An etching plate covered with powder resin
Other uses that are not based on friction:
Fine art uses rosin for tempera emulsions and as painting-medium component for oil paintings. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is soluble in oil of turpentine and turpentine substitute, and needs to be warmed.
In a printmaking technique, aquatint rosin is used on the etching plate in order to create surfaces in gray tones.
In archery, when a new bowstring is being made or waxed for maintenance purposes, rosin may be present in the wax mixture. 
This provides an amount of tackiness to the string to hold rosins's constituent strands together and reduce wear and fraying.
Dog groomers use powdered rosin to aid in removal of excess hair from deep in the ear canal.
Some brands of fly paper use a solution of rosin and rubber as the adhesive.
Rosin is sometimes used as an ingredient in dubbing wax used in fly tying.
Rosin is used hot to de-encapsulate epoxy integrated circuits.
Rosin can be mixed with beeswax and a small amount of linseed oil to affix reeds to reed blocks in accordions.
Rosin potatoes can be cooked by dropping potatoes into boiling rosin and cooking until they float to the surface.
Rosin and rosins's derivatives also exhibit wide-ranging pharmaceutical applications. Rosin derivatives show excellent film forming and coating properties.
They are also used for tablet film and enteric coating purpose. Rosins have also been used to formulate microcapsules and nanoparticles.

Glycerol, sorbitol, and mannitol esters of rosin are used as chewing gum bases for medicinal applications. 
The degradation and biocompatibility of rosin and rosin-based biomaterials has been examined in vitro and ex vivo.

What is Gum Rosin?
Rosin, also called colophony or Greek pitch (Latin: pix græca), is a solid form of resin obtained from pines and some other plants, mostly conifers, produced by heating fresh liquid resin to vaporize the volatile liquid terpene components. 
It is semi-transparent and varies in color from yellow to black. 
At room temperature rosin is brittle, but Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl melts at stove-top temperature. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl chiefly consists of various resin acids, especially abietic acid. T
he term "colophony" comes from colophonia resina, Latin for "resin from Colophon," an ancient Ionic city.
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl becomes sticky when warm and has a faint pinelike odour. 
Gum rosin consists of the residue obtained upon distillation of the oleoresin (a natural fluid) from pine trees (the volatile component is spirit of turpentine); wood rosin, obtained by solvent extraction of the stumps, is usually of a darker colour.

Gum Rosin Uses
Most rosin is used in a chemically modified form rather than in the raw state in which it is obtained. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl consists primarily of a mixture of abietic-type and pimaric-type acids with smaller amounts of neutral compounds. 

This intrinsic acidity, coupled with other chemical properties, enables it to be converted to a Large number of downstream derivatives which are used in a wide range of applications. 
The derivatives include salts, esters and maleic anhydride adducts, and hydrogenated, disproportionated and polymerized rosins. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl's most important uses are in the manufacture of adhesives, paper sizing agents, printing inks, solders and fluxes, various surface coatings, insulating materials for the electronics industry, synthetic rubber, chewing gums and soaps and detergents.
Rosin and rosins chemical derivatives are used chiefly to make soaps, varnishes, sealing wax, printing inks, driers, sizes for paper, adhesives, binders, soldering fluxes, gloss oils for paints, and pitch for casks. 
Rosin is also used on bows of violins and other stringed instruments, on the shoes of dancers, and on floors of studios and stages to prevent slipping.

Gum Rosin Applications
Foodstuff Industry - Gum Rosin is firstly converted into hydrogenated rosin, and then used to produce chewing gum
Paints & Coating Industry - Rosin is a basic material for paint industry because rosin is easy to dissolve in alcohol, gasoline, turpentine and others organic solvent. 
Rosin always is converted to resinate, and then refine with drying oil such as tung oil and mix with volatility solvent to produce various lacquers. 
Rosin also take important role in producing road coating, rosin firstly converted to rosin malefic ester or polymerized rosin or disproportionated rosin Polyols ester, and then used to make thermoplastic coating for road sign inunction.
Metal Processing Industry - Rosin mainly is used as solding aid and metal polishing agent. 
Rosin is a kind of weak acidity matter, rosin can remove oxidation film from metal surface and slightly erode the surface of metal, and therefore, lots of solding aid agents contain rosin.
Construction Materials Industry - Rosin mainly is used as concrete frothing agent and floor tiling adhesive.
Papermaking Industry - Most rosin was applied to papermaking industry as sizing agent. Rosin paper sizing agent can prevent printing oil soaking and dispersing from paper, improves the strength and smoothness of paper; enhances the anti-abrasion of paper. 
But crystal rosin is unfit for making paper sizing agent due to difficulty of saponification, subsequently makes spot on the paper; sometimes even makes the pipe jam in paper sizing agent producing.
Printing Inks Industry - Rosin mainly act as color carrier and enhance color adhesive ability in printing ink. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl takes about 7% of quality of printing oil in China. 
Rosin is converted into modified phenolic rosin with softening point of 160 to 175 Celsius degrees and below 20 acid value when Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is used in offset printing ink producing. 
In photogravure printing ink producing, rosin firstly is converted into metal salt rosin with softening point of 125 to 135 Celsius degrees and below 95 acid value. 
For polymerized rosin, rosin can be used to producing various special printing ink.
Bactericide Industry - Rosin can be converted into abietylamine acetate for killing algae, bacteria, mildew, mollusk and others pest.
Adhesives & Sealants Industry - Rosin was widely used as an ingredient of some kind of adhesive; especially in heat melt adhesive, pressure sensitive adhesive and rubber adhesive. 
Rosin mainly is used to enhance the strength, plasticity and viscosity of adhesive.
Electrical Equipment Industry - Rosin is used as insulation material in electric equipment industry; China has long history of applying rosin as insulation material in cable industry. 
Rosin also can mix with bakelite and others artificial resin to soak and besmear electric loop.
Fine chemicals Industry - Abietic acid is the main ingredient of rosin, Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl can be synthesized with others matter to produce series optics reactive materials and biotic reactive materials; these materials have special function for human and others organism.
Synthetic Rubber Industry - Rosin is used as softener in synthetic rubber industry; Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl enhances the plasticity, tear strength, heat resistance, flexibility and anti-abrasion of synthetic rubber; also rosin can be use as dispersant and emulsification in synthetic rubber industry. 
After seventies of twenty century, about 20% of total annual output of rosin was used synthetic rubber industry.

Rosin Properties
Melting point:70-72°C
Density 1,07 g/cm3
Flash point:180°C
solubility chloroform: 0.1 g/mL, clear, strongly yellow
form Powder/Solid
color Dark yellow
Specific Gravity1.07～1.08
Water Solubility Soluble in alcohol, benzene, ether. Insoluble in water
Stability:Stable. Combustible. Incompatible with oxidizing agents.

Properties
Pharmaceutical rosin
Rosin is brittle and friable, with a faint piny odor. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is typically a glassy solid, though some rosins will form crystals, especially when brought into solution.
The practical melting point varies with different specimens, some being semi-fluid at the temperature of boiling water, others melting at 100 °C to 120 °C. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is very flammable, burning with a smoky flame, so care should be taken when melting Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is soluble in alcohol, ether, benzene and chloroform.

Rosin consists mainly of abietic acid, and combines with caustic alkalis to form salts (rosinates or pinates) that are known as rosin soaps. 
In addition to its extensive use in soap making, rosin is largely employed in making varnishes (including fine violin varnishes), sealing wax and various adhesives. 
Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is also used for preparing shoemakers' wax, for pitching lager beer casks, and numerous other purposes such as providing backing surfaces to tin ware, copper ware, or even silver and gold vessels when embossing or engraving them. 
Its relatively low melting point, and firm solid form allows liquid rosin to be poured into the vessel, and when cooled allows embossing or engraving of the vessel without deforming the vessel - even if Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl has a skin which is quite thin. 
Afterwards, the object can be reheated in an oven, and the rosin poured out for reuse. 
Any remaining rosin film can easily be rinsed away with alcohol or other solvents.

Rosin is also sometimes used as internal reinforcement for very thin skinned metal objects - things like silver, copper or tin plate candlesticks, or sculptures, where Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is simply melted, poured into a hollow thin-skinned object, and left to harden.
Prolonged exposure to rosin fumes released during soldering can cause occupational asthma (formerly called colophony disease in this context) in sensitive individuals, although Beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl is not known which component of the fumes causes the problem.

The type of rosin used with bowed string instruments is determined by the diameter of the strings. 
Generally this means that the larger the instrument is, the softer the rosin should be. 
For instance, double bass rosin is generally soft enough to be pliable with slow movements. 
A cake of bass rosin left in a single position for several months will show evidence of flow, especially in warmer weather.
Prolonged exposure to rosin, by handling rosin-coated products, such as laser printer or photocopying paper, can give rise to a form of industrial contact dermatitis.

Production
Various types of rosin for violins, violas and cellos
A piece of rosin for violins, violas and cellos
Rosin is the resinous constituent of the oleo-resin exuded by various species of pine, known in commerce as crude turpentine. 
The separation of the oleo-resin into the essential oil (spirit of turpentine) and common rosin is accomplished by distillation in large copper stills. 
The essential oil is carried off at a temperature of between 100 °C (212 °F)° and 160 °C (320 °F), leaving fluid rosin, which is run off through a tap at the bottom of the still, and purified by passing through straining wadding. 
Rosin varies in color, according to the age of the tree from which the turpentine is drawn and the degree of heat applied in distillation, from an opaque, almost pitch-black substance through grades of brown and yellow to an almost perfectly transparent colorless glassy mass. 
The commercial grades are numerous, ranging by letters from A (the darkest) to N (extra pale), superior to which are W (window glass) and WW (water-white) varieties, the latter having about three times the value of the common qualities.

Computed Properties
    XLogP3: -0.1    
Hydrogen Bond Donor Count:4    
Hydrogen Bond Acceptor Count: 6    
Rotatable Bond Count: 5    
Exact Mass: 296.12598835    
Monoisotopic Mass:296.12598835    
Topological Polar Surface Area:99.4 Ų    
Heavy Atom Count:21    
Formal Charge: 0    
Complexity: 328    
Isotope Atom Count: 0    
Defined Atom Stereocenter Count: 5    
Undefined Atom Stereocenter Count:0    
Defined Bond Stereocenter Count: 1    
Undefined Bond Stereocenter Count: 0    
Covalently-Bonded Unit Count: 1    
Compound Is Canonicalized:Yes

Rosin Wax
This sample of blonde wax is a mixture of rosin (a brittle, dusty and solid amber-coloured resin derived from pines trees) and beeswax. 
The rosin, also known as colophony or Greek pitch, gives this wax its tackiness. 
It is made by heating fresh liquid tree sap (oleo-resin) to remove the volatile liquid terpene compounds. 
If you scratch off a small amount of this substance and warm it up between your fingers, it smells like a mixture of pine and turpentine.
Rosin typically varies in colour from very pale and transparent to dark brown or yellow depending on the age of tree the sap is extracted from and the temperature to which it is heated. 
Rosin is crucial for creating sound in string instruments as it allows the horsehair bowstrings to grip the metal strings of the instrument and ‘make them speak’. 
The different colours of rosin are said to produce different tones as a result of their differential stickiness, and as such, there are many different types formulated for different kinds of tone (subtle or aggressive), particular kinds of playing conditions like humidity, or specific instruments (violin verse cello).

Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odor No data available
c) Odor Threshold No data available
d) pH No data available
e) Meltingpoint/freezing point:114 - 116 °C
f) Initial boiling point
g) Flash point No data available
h) Evaporation rate No data available
i) Flammability (solid, gas) No data available
j) Upper/lower flammability or explosive limits No data available
k) Vapor pressure No data available
l) Vapor density No data available
m) Relative density No data available
n) Water solubility No data available
o) Partition coefficient:n-octanol/water No data available
p) Autoignition temperature No data available
Sigma- SMB00582 Page 5 of 7
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Stability and reactivity
Reactivity
The following applies in general to flammable organic substances and mixtures
in correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.
Chemical stability
The product is chemically stable under standard ambient conditions (room temperature) .
Possibility of hazardous reactions : No data available
Conditions to avoid: no information available
Incompatible materials: Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides
Other decomposition products

First aid measures
Description of first-aid measures
If inhaled
After inhalation: fresh air.
In case of skin contact
In case of skin contact: Take off immediately all contaminated clothing. 
Rinse skin with water/ shower.
In case of eye contact
After eye contact: rinse out with plenty of water. 
Remove contact lenses.
If swallowed
After swallowing: make victim drink water (two glasses at most). 
Consult doctor if feeling unwell.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling 
Indication of any immediate medical attention and special treatment needed
No data available

Firefighting measures
Extinguishing media
Suitable extinguishing media
Water Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media
For this substance/mixture no limitations of extinguishing agents are given.
Special hazards arising from the substance or mixture
Carbon oxides
Combustible.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters:
In the event of fire, wear self-contained breathing apparatus.
Further information
Prevent fire extinguishing water from contaminating surface water or the ground water system.

Accidental release measures
Personal precautions, protective equipment and emergency procedures
Advice for non-emergency personnel: 
Avoid inhalation of dusts.
Evacuate the danger area, observe emergency procedures, consult an expert.

Environmental precautions
Do not let product enter drains.

Methods and materials for containment and cleaning up
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions
Take up dry.
Dispose of properly. 
Clean up affected area. Avoid generation of dusts.

Handling and storage
Conditions for safe storage, including any incompatibilities
Tightly closed. 
Dry.
Recommended storage temperature 2 - 8 °C
Hygroscopic.

Alternative Names
ROSIN
85026-55-7(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol
beta-D-Glucopyranoside,(2E)-3-phenyl-2-propenyl
69306-80-5
beta-D-Glucopyranoside, 3-phenyl-2-propenyl, (E)-
CHEMBL4175856
Rosin, >=95% (HPLC)
SCHEMBL15641934
SCHEMBL15641935
DTXSID60904535
HY-N0508
ZINC4096342
3-Phenylallyl beta-D-glucopyranoside
MFCD23103373
AKOS016009311
Rosin soap (disproportionated) solution
3-Phenyl-2-propenylbeta-D-glucopyranoside
3-Phenyl-2-propenyl beta-D-glucopyranoside
CS-0009048
N2694
(E)-3-phenyl-2-propenyl beta-D-glucopyranoside
(2E)-3-Phenyl-2-propen-1-yl -D-glucopyranoside
306P805
beta-D-Glucopyranoside, (2E)-3-phenyl-2-propenyl