Salicin

Short description: Chemical compound

Salicin[1]

Names
IUPAC name

2-(Hydroxymethyl)phenyl β-D-glucopyranoside

Systematic IUPAC name

(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol

Other names

Salicin; D-(−)-Salicin; Salicoside

Identifiers

CAS Number

* 138-52-3 Y

3D model (JSmol)

* Interactive image

Abbreviations  | Glc(b)-O-Ph(2-CH2OH)
ChemSpider |

* 388601 N

KEGG |

* C01451 N

PubChem CID

* 439503

RTECS number |

* LZ5901700

UNII |

* 4649620TBZ Y

InChI

* InChI=1/C13H18O7/c14/h1-4,9-18H,5-6H2

SMILES

* OCc1ccccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Properties

Chemical formula

| C13H18O7
Molar mass | 286.280 g·mol−1
Appearance  | White crystals
Density | 1.434 g/cm3[2]
Melting point |  207 °C (405 °F; 480 K)[2]
Boiling point | 240 decomp.[2]

Solubility in water

| 43 g/L
Solubility in Ethanol | 3 g/L
Solubility in DMSO | 20 g/L
Solubility in dimethyl formamide | 30 g/L
Hazards
Main hazards | Skin sensitizer / Contact dermatitis[3]
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H317

GHS precautionary statements

| P261, P272, P280, P302+352, P333+313, P362, P363, P501
NFPA 704 (fire diamond)  |

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Salicin is an alcoholic β-glucoside. Salicin is produced in (and named after) willow (Salix) bark. It is a biosynthetic precursor to salicylaldehyde.[4]

## Medicinal aspects

Salicin is found in the bark of and leaves of willows, poplars and various other plants. Derivates are found in castoreum. Salicin from meadowsweet was used in the synthesis of aspirin (acetylsalicylic acid),[5] in 1899 by scientists at Bayer. Salicin tastes bitter like quinine.[6]

Salicin may cause an allergic skin reaction (skin sensitization; category 1).[3]

Mild side effects are standard, with rare occurrences of nausea, vomiting, rash, dizziness and breathing problems. Overdose from high quantities of salicin can be toxic, damaging kidneys, causing stomach ulcers, diarrhea, bleeding or digestive discomfort. Some people may be allergic or sensitive to salicylates and suffer reactions similar to those produced by aspirin. People should not take salicin if they have asthma, diabetes, gout, gastritis, hemophilia, stomach ulcers; also contraindicated are children under 16, and pregnant and breastfeeding women.[7]

## References

1. ↑ Merck Index, 11th Edition, 8293
2. ↑ 2.0 2.1 2.2 Haynes, William M., ed (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.312. ISBN 9781498754293.
3. ↑ 3.0 3.1 PubChem
4. ↑ Pasteels, J. M.; Rowell-Rahier, M.; Braekman, J. C.; Dupont, A. (1983). "Salicin from host plant as precursor of salicylaldehyde in defensive secretion of Chrysomeline larvae". Physiological Entomology 8 (3): 307–314. doi:10.1111/j.1365-3032.1983.tb00362.x. https://dipot.ulb.ac.be/dspace/bitstream/2013/95098/4/ac2db4af-9a60-4c77-bdb4-6fa9e75d3003.txt.
5. ↑ "History of Aspirin". http://inventors.about.com/library/inventors/blaspirin.htm.
6. ↑ Daniells, S (2006-10-09). "Symrise explores cheaper alternatives in bitter-maskers". www.foodnavigator.com. http://www.foodnavigator.com/Science-Nutrition/Symrise-explores-cheaper-alternatives-in-bitter-maskers.
7. ↑ "Willow bark | University of Maryland Medical Center". http://umm.edu/health/medical/altmed/herb/willow-bark.

* v
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* e

Analgesics (N02A, N02B)

Opioids|

| Opiates/opium|

* Codeine# (+paracetamol, +aspirin)
* Morphine# (+naltrexone)
* Opium
* Laudanum
* Paregoric

|

Semisynthetic|

* Acetyldihydrocodeine
* Benzylmorphine
* Buprenorphine (+naloxone)
* Desomorphine
* Diamorphine (heroin)
* Dihydrocodeine (+paracetamol)
* Dihydromorphine
* Ethylmorphine
* Hydrocodone (+paracetamol, +ibuprofen, +aspirin)
* Hydromorphinol
* Hydromorphone
* Nicocodeine
* Nicodicodine
* Nicomorphine
* Oxycodone (+paracetamol, +aspirin, oxycodone/ibuprofen

Synthetic|

* Alfentanil
* Alphaprodine
* Anileridine
* Butorphanol
* Carfentanil
* Dextromoramide
* Dextropropoxyphene
* Dezocine
* Fentanyl# (+fluanisone)
* Ketobemidone
* Levorphanol
* Lofentanil
* Meptazinol
* Methadone#
* Nalbuphine
* NFEPP
* Pentazocine
* Pethidine (meperidine)
* Phenadoxone
* Phenazocine
* Piminodine
* Piritramide
* Propiram
* Remifentanil
* Sufentanil
* Tapentadol
* Tilidine
* Tramadol

Paracetamol-type|

* Acetanilide‡
* Bucetin‡
* Butacetin‡
* Paracetamol (acetaminophen)#
* Parapropamol‡
* Phenacetin‡
* Propacetamol‡

NSAIDs|

| Propionates|

* Fenoprofen
* Flurbiprofen
* Ibuprofen#
* Ketoprofen
* Naproxen
* Oxaprozin

|

Oxicams|

* Meloxicam
* Piroxicam

Acetates|

* Diclofenac
* Indometacin
* Ketorolac
* Nabumetone
* Sulindac
* Tolmetin

COX-2 inhibitors|

* Celecoxib
* Etoricoxib
* Lumiracoxib
* Parecoxib
* Rofecoxib ‡
* Valdecoxib ‡

Fenamates|

* Meclofenamic acid
* Mefenamic acid

Salicylates|

* Aspirin (acetylsalicylic acid)# (+paracetamol/caffeine)
* Benorylate
* Diflunisal
* Ethenzamide
* Magnesium salicylate
* Salicin
* Salicylamide
* Salsalate
* Wintergreen (methyl salicylate)

Pyrazolones|

* Aminophenazone‡
* Ampyrone
* Metamizole (dipyrone)
* Nifenazone
* Phenazone
* Propyphenazone (+paracetamol/caffeine)

Others|

* Glafenine

Cannabinoids|

* Cannabidiol
* Cannabis
* Nabilone
* Nabiximols
* Tetrahydrocannabinol (dronabinol)

Ion channel
modulators|

| Calcium blockers|

* Gabapentin
* Gabapentin enacarbil
* Mirogabalin
* Pregabalin
* Ziconotide

|

Sodium blockers|

* Carbamazepine
* Lacosamide
* Local anesthetics (e.g., cocaine, lidocaine)
* Mexiletine
* Nefopam
* Tricyclic antidepressants (e.g., amitriptyline#)

* Nav1.7/1.8-selective: DSP-2230§
* Funapide§
* PF-05089771§

Potassium openers|

* Flupirtine

Myorelaxants|

* Carisoprodol
* Chlorzoxazone
* Cyclobenzaprine
* Mephenoxalone
* Methocarbamol
* Orphenadrine

Others|

* Analgesic adjuvant
* Analgecine
* Camphor
* Capsaicin
* Clonidine
* Ketamine
* Menthol
* Methoxyflurane
* Nefopam
* Proglumide
* Tricyclic antidepressants (e.g., amitriptyline#)

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

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Nonsteroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)

Pyrazolones /
Pyrazolidines|

* Aminophenazone
* Ampyrone
* Azapropazone
* Clofezone
* Difenamizole
* Famprofazone
* Feprazone
* Kebuzone
* Metamizole
* Mofebutazone
* Morazone
* Nifenazone
* Oxyphenbutazone
* Phenazone
* Phenylbutazone
* Propyphenazone
* Sulfinpyrazone
* Suxibuzone‡

Salicylates|

* Aspirin (acetylsalicylic acid)#
* Aloxiprin
* Benorylate
* Carbasalate calcium
* Diflunisal
* Dipyrocetyl
* Ethenzamide
* Guacetisal
* Magnesium salicylate
* Methyl salicylate
* Salsalate
* Salicin
* Salicylamide
* Salicylic acid (salicylate)
* Sodium salicylate

Acetic acid derivatives
and related substances|

* Aceclofenac
* Acemetacin
* Alclofenac
* Amfenac
* Bendazac
* Bromfenac
* Bumadizone
* Bufexamac
* Diclofenac
* Difenpiramide
* Etodolac
* Felbinac
* Fenclozic acid
* Fentiazac
* Indometacin
* Indometacin farnesil
* Isoxepac
* Ketorolac
* Lonazolac
* Oxametacin
* Prodolic acid
* Proglumetacin
* Sulindac
* Tiopinac
* Tolmetin
* Zomepirac†

Oxicams|

* Ampiroxicam
* Droxicam
* Isoxicam
* Lornoxicam
* Meloxicam
* Piroxicam
* Tenoxicam

Propionic acid derivatives
(profens)|

* Alminoprofen
* Benoxaprofen†
* Carprofen‡
* Dexibuprofen
* Dexketoprofen
* Fenbufen
* Fenoprofen
* Flunoxaprofen
* Flurbiprofen
* Ibuprofen#
* Ibuproxam
* Indoprofen†
* Ketoprofen
* Loxoprofen
* Miroprofen
* Naproxen
* Oxaprozin
* Pirprofen
* Suprofen
* Tarenflurbil
* Tepoxalin‡
* Tiaprofenic acid
* Vedaprofen‡
* Zaltoprofen
* COX-inhibiting nitric oxide donator: Naproxcinod

N-Arylanthranilic acids
(fenamates)|

* Azapropazone
* Clonixin
* Etofenamate
* Flufenamic acid
* Flunixin
* Meclofenamic acid
* Mefenamic acid
* Morniflumate
* Niflumic acid
* Tolfenamic acid
* Flutiazin

Coxibs|

* Apricoxib
* Celecoxib
* Cimicoxib‡
* Deracoxib‡
* Etoricoxib
* Firocoxib‡
* Lumiracoxib†
* Mavacoxib‡
* Parecoxib
* Robenacoxib‡
* Rofecoxib†
* Valdecoxib†

Other|

* Aminopropionitrile
* Benzydamine
* Chondroitin sulfate
* Diacerein
* Fluproquazone
* Glucosamine
* Glycosaminoglycan
* Hyperforin
* Nabumetone
* Nimesulide
* Oxaceprol
* Proquazone
* Superoxide dismutase/Orgotein
* Tenidap

Items listed in bold indicate initially developed compounds of specific groups. #WHO-EM †Withdrawn drugs. ‡Veterinary use medications.

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Glycosides

Bond|

* O-glycosidic bond
* N-glycosidic bond
* S-glycosidic bond
* C-glycosidic bond

Geometry|

* α-Glycoside
* β-Glycoside
* 1,4-Glycoside
* 1,6-Glycoside

Glycone|

* Fructoside
* Galactoside
* Glucoside
* Glucuronide
* Rhamnoside
* Riboside

Aglycone|

* Alcoholic glycoside
* Cardiac glycoside
* Bufadienolide
* Cardenolide
* Cyanogenic glycoside
* Glycosylamine
* Phenolic glycoside
* Anthraquinone glycoside
* Coumarin glycoside
* Flavonoid glycoside
* Saponin
* Steviol glycoside
* Thioglycoside

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Salicylates

* Salicylic acid
* Aspirin
* Aloxiprin
* Methyl salicylate
* Magnesium salicylate
* Ethyl salicylate
* Bismuth subsalicylate
* Sodium salicylate
* Salicylamide
* Salicin
* Benorilate
* Salsalate
* Ethenzamide
* Diflunisal
* Trolamine salicylate
* Homosalate
* Salicylmethylecgonine
* Octyl salicylate
* Aluminon
* Benzyl salicylate
* Copper aspirinate
* Potassium salicylate

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Prostanoid signaling modulators

Receptor
(ligands)|

| DP (D2)|

| DP1|

* Agonists: Prostaglandin D2
* Treprostinil

* Antagonists: Asapiprant
* Laropiprant
* Vidupiprant

|

DP2|

* Agonists: Indometacin
* Prostaglandin D2

* Antagonists: ADC-3680
* AZD-1981
* Bay U3405
* Fevipiprant
* MK-1029
* MK-7246
* QAV-680
* Ramatroban
* Setipiprant
* Timapiprant
* TM30089
* Vidupiprant

EP (E2)|

| EP1|

* Agonists: Beraprost
* Enprostil
* Iloprost (ciloprost)
* Latanoprost
* Lubiprostone
* Misoprostol
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* Sulprostone

* Antagonists: AH-6809
* ONO-8130
* SC-19220
* SC-51089
* SC-51322

|

EP2|

* Agonists: Butaprost
* Misoprostol
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* Treprostinil

* Antagonists: AH-6809
* PF-04418948
* TG 4-155

EP3|

* Agonists: Beraprost
* Carbacyclin
* Cicaprost
* Enprostil
* Iloprost (ciloprost)
* Isocarbacyclin
* Latanoprost
* Misoprostol
* Prostaglandin D2
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* Remiprostol
* Sulprostone

* Antagonists: L-798106

EP4|

* Agonists: Lubiprostone
* Misoprostol
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* TCS-2510

* Antagonists: Grapiprant
* GW-627368
* L-161982
* ONO-AE3-208

Unsorted|

* Agonists: 16,16-Dimethyl Prostaglandin E2
* Aganepag
* Carboprost
* Evatanepag
* Gemeprost
* Nocloprost
* Omidenepag
* Prostaglandin F2α (dinoprost)
* Simenepag
* Taprenepag

FP (F2α)|

* Agonists: Alfaprostol
* Bimatoprost
* Carboprost
* Cloprostenol
* Enprostil
* Fluprostenol
* Latanoprost
* Prostaglandin D2
* Prostaglandin F2α (dinoprost)
* Sulotroban
* Tafluprost
* Travoprost
* Unoprostone

IP (I2)|

* Agonists: ACT-333679
* AFP-07
* Beraprost
* BMY-45778
* Carbacyclin
* Cicaprost
* Iloprost (ciloprost)
* Isocarbacyclin
* MRE-269
* NS-304
* Prostacyclin (prostaglandin I2, epoprostenol)
* Prostaglandin E1 (alprostadil)
* Ralinepag
* Selexipag
* Taprostene
* TRA-418
* Treprostinil

* Antagonists: RO1138452

TP (TXA2)|

* Agonists: Carbocyclic thromboxane A2
* I-BOP
* Thromboxane A2
* U-46619
* Vapiprost

* Antagonists: 12-HETE
* 13-APA
* AA-2414
* Argatroban
* Bay U3405
* BMS-180,291
* Daltroban
* Domitroban
* EP-045
* GR-32191
* ICI-185282
* ICI-192605
* Ifetroban
* Imitrodast
* L-655240
* L-670596
* Linotroban
* Mipitroban
* ONO-3708
* ONO-11120
* Picotamide
* Pinane thromboxane A2
* Ramatroban
* Ridogrel
* S-145
* Samixogrel
* Seratrodast
* SQ-28,668
* SQ-29,548
* Sulotroban
* Terbogrel
* Terutroban
* TRA-418

Unsorted|

* Arbaprostil
* Ataprost
* Ciprostene
* Clinprost
* Cobiprostone
* Delprostenate
* Deprostil
* Dimoxaprost
* Doxaprost
* Ecraprost
* Eganoprost
* Enisoprost
* Eptaloprost
* Esuberaprost
* Etiproston
* Fenprostalene
* Flunoprost
* Froxiprost
* Lanproston
* Limaprost
* Luprostiol
* Meteneprost
* Mexiprostil
* Naxaprostene
* Nileprost
* Nocloprost
* Ornoprostil
* Oxoprostol
* Penprostene
* Pimilprost
* Piriprost
* Posaraprost
* Prostalene
* Rioprostil
* Rivenprost
* Rosaprostol
* Spiriprostil
* Tiaprost
* Tilsuprost
* Tiprostanide
* Trimoprostil
* Viprostol

Enzyme
(inhibitors)|

| COX
(PTGS)|

* Salicylic acids: Aloxiprin
* Aspirin (acetylsalicylic acid)
* Benorilate (benorylate)
* Carbasalate calcium
* Diflusinal
* Dipyrocetyl
* Ethenzamide
* Guacetisal
* Magnesium salicylate
* Mesalazine (5-aminosalicylic acid)
* Methyl salicylate
* Salacetamide
* Salicin
* Salicylamide
* Salicylate (salicylic acid)
* Salsalate
* Sodium salicylate
* Triflusal; Acetic acids: Aceclofenac
* Acemetacin
* Aclofenac
* Amfenac
* Alclofenac
* Bendazac
* Bromfenac
* Bufexamac
* Bumadizone
* Cinmetacin
* Clometacin
* Diclofenac
* Difenpiramide
* Etodolac
* Felbinac
* Fenclofenac
* Fentiazac
* Glucametacin
* Indometacin (indomethacin)
* Indometacin farnesil
* Ketorolac
* Lonazolac
* Mofezolac
* Nabumetone
* Oxametacin
* Oxindanac
* Proglumetacin
* Sulindac
* Sulindac sulfide
* Tolmetin
* Zidometacin
* Zomepirac; Propionic acids: Alminoprofen
* Benoxaprofen
* Bucloxic acid (blucloxate)
* Butibufen
* Carprofen
* Dexibuprofen
* Dexindoprofen
* Dexketoprofen
* Fenbufen
* Fenoprofen
* Flunoxaprofen
* Flurbiprofen
* Ibuprofen
* Ibuproxam
* Indoprofen
* Ketoprofen
* Loxoprofen
* Miroprofen
* Naproxen
* Naproxcinod
* Oxaprozin
* Pirprofen
* Pranoprofen
* Suprofen
* Tarenflurbil
* Tepoxalin
* Tiaprofenic acid (tiaprofenate)
* Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate)
* Floctafenic acid (floctafenate)
* Flufenamic acid (flufenamate)
* Meclofenamic acid (meclofenamate)
* Mefenamic acid (mefenamate)
* Morniflumic acid (morniflumate)
* Niflumic acid (niflumate)
* Talinflumic acid (talinflumate)
* Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone
* Dipyrone
* Isopyrin
* Oxyphenbutazone
* Phenylbutazone; Enolic acids (oxicams): Ampiroxicam
* Droxicam
* Enolicam
* Isoxicam
* Lornoxicam
* Meloxicam
* Piroxicam
* Tenoxicam; 4-Aminoquinolines: Antrafenine
* Floctafenine
* Glafenine; Quinazolines: Fluproquazone
* Proquazone; Aminonicotinic acids: Clonixeril
* Clonixin
* Flunixin; Sulfonanilides: Flosulide
* Nimesulide; Aminophenols (anilines): Acetanilide
* AM-404 (N-arachidonoylaminophenol)
* Bucetin
* Paracetamol (acetaminophen)
* Parapropamol
* Phenacetin
* Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib
* Celecoxib
* Cimicoxib
* Deracoxib
* Etoricoxib
* Firocoxib
* Lumiracoxib
* Mavacoxib
* Parecoxib
* Polmacoxib
* Robenacoxib
* Rofecoxib
* Tilmacoxib
* Valdecoxib; Others/unsorted: Anitrazafen
* Clobuzarit
* Curcumin
* DuP-697
* FK-3311
* Flumizole
* FR-122047
* Glimepiride
* Hyperforin
* Itazigrel
* L-655240
* L-670596
* Licofelone
* Menatetrenone (vitamin K2)
* NCX-466
* NCX-4040
* NS-398
* Pamicogrel
* Resveratrol
* Romazarit
* Rosmarinic acid
* Rutecarpine
* Satigrel
* SC-236
* SC-560
* SC-58125
* Tenidap
* Tiflamizole
* Timegadine
* Trifenagrel
* Tropesin

|

PGD2S|

* Retinoids
* Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)

PGES|

HQL-79

PGFS|

Bimatoprost

PGI2S|

Tranylcypromine

TXAS|

* Camonagrel
* Dazmegrel
* Dazoxiben
* Furegrelate
* Isbogrel
* Midazogrel
* Nafagrel
* Nicogrelate
* Ozagrel
* Picotamide
* Pirmagrel
* Ridogrel
* Rolafagrel
* Samixogrel
* Terbogrel
* U63557A

Others|

* Precursors: Linoleic acid
* γ-Linolenic acid (gamolenic acid)
* Dihomo-γ-linolenic acid
* Diacylglycerol
* Arachidonic acid
* Prostaglandin G2
* Prostaglandin H2

See also
Receptor/signaling modulators
Leukotriene signaling modulators
Nuclear receptor modulators

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Original source: https://en.wikipedia.org/wiki/Salicin. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Salicin&oldid=810581"
*[CID]: Compound ID
*[H317]: May cause an allergic skin reaction
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P333+313]: If skin irritation or a rash occurs: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P363]: Wash contaminated clothing before reuse
*[P501]: Dispose of contents/container to …
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[DP (D2)]: Prostaglandin D2 receptor
*[DP1]: Prostaglandin D2 receptor 1
*[DP2]: Prostaglandin D2 receptor 2
*[EP (E2)]: Prostaglandin E2 receptor
*[EP1]: Prostaglandin EP1 receptor
*[EP2]: Prostaglandin EP2 receptor
*[EP3]: Prostaglandin EP3 receptor
*[EP4]: Prostaglandin EP4 receptor
*[FP (F2α)]: Prostaglandin F receptor
*[IP (I2)]: Prostacyclin receptor
*[TP (TXA2)]: Thromboxane receptor
*[COX]: Cyclooxygenase
*[PTGS]: prostaglandin G/H synthase
*[PGD2S]: Prostaglandin D synthase
*[PGES]: Prostaglandin E synthase
*[PGFS]: Prostaglandin F synthase
*[PGI2S]: Prostacyclin synthase
*[TXAS]: Thromboxane A synthase