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100% Pure Natural Chili Pepper Extract Capsaicin 99% Powder
Cas No: 404-86-4
USD $ 0.38-0.43 / Gram 10 Gram 100 Kilogram/Year Xi'an Quanao Biotech Co., Ltd. Contact Supplier
High purity Chili Pepper Extract Nature Capsaicin
Cas No: 404-86-4
No Data 1 Gram 50 Kilogram/Month AmoyChem Co.,Ltd Contact Supplier
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USD $ 2700.0-2800.0 / Kilogram 1 Kilogram 5 Metric Ton/Month Kono Chem Co.,Ltd Contact Supplier
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E-0351 Capsaicin
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USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
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USD $ 70.0-130.0 / Kilogram 1 Kilogram 99999 Kilogram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
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404-86-4 Usage

Chemical Synthesis

From 3-chloro-2-isopropyltetrahydropyran; biosynthesis from Capsicum frutescens; separation from cis-capsaicin, pelargonic acid vanillamide and dihydrocapsaicin; reaction of capsaicin

Indications

Capsaicin (Zostrix) is approved for the relief of pain following herpes zoster infection (postherpetic neuralgia). The drug depletes neurons of substance P, an endogenous neuropeptide that may mediate cutaneous pain. It is applied to affected skin after open lesions have healed. Local irritation is common.

Uses

As a tool in neurobiological research.

Uses

Capsaicin is used in many topical ointments used to relieve the pain of peripheral neuropathy (treatment of pain in the nerve endings near the surface of the skin).

History

Capsaicin is a naturally occurring substance that is responsible for the burning, pungent sensation associated with the ingestion of hot peppers from the Capsicum genus. The effect elicited by these peppers is at the origin of the name Capsicum, which derives from the Greek kapto, meaning “to bite”. Hot peppers are a native plant from the American tropics and their use can be traced back to the Aztec and Inca civilizations. The Aztecs named them “chilies” and used them for culinary purposes. After discovery of the New World, chili pods were introduced in Europe and their cultivation expanded to other parts of the globe. Nowadays, hot peppers are found in nearly every country and are an important part of the culinary tradition of many different cultures. The active component of chili peppers was initially isolated by J. C. Thresh in 1846. The compound was named “capsaicin” and its chemical structure was later determined by E. K. Nelson in 1919. The complete chemical synthesis of 8-methyl-N- vanillyl-6-nonenamide (capsaicin’s IUPAC* name) was reported in 1930 by Spath &Darling. In the 1960’s, Japanese investigators identified additional substances from Capsicum extracts with similar chemical and pharmacological properties that were termed “capsaicinoids”. Currently, this family of chemical analogues includes both natural (homodihydrocapsaicin, dihydrocapsaicin, nordihydrocapsaicin, homocapsaicin and capsaicin) and synthetic (nonivamide) members.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Biological Activity

Prototypic vanilloid receptor agonist (pEC 50 values are 7.97 and 7.10 at rat and human VR1 receptors respectively). Excites a subset of primary afferent sensory neurons, with subsequent antinociceptive and anti-inflammatory effects. Reversibly inhibits aggregation of platelets. Also available as part of the Vanilloid TRPV1 Receptor Tocriset? .

Uses

Capsaicin is what makes chili peppers hot. It is an irritant.for mam- mals, but not for birds. This may be because birds spread the seeds better than mammals. It causes a burning sensation in any mam- malian tissue with which it comes in contact. Capsaicin is a nonpolar molecule; it dissolves in fats and oils, not in water. This is why water does not take away the burning sensation, but whole milk or other fat-containing liquids or foods will. As an ingredient in medicines, capsaicin is used to relieve pain from arthritis, muscle aches, and sprains. It is a rubefacient, meaning it dilates blood vessels. The heat effect overwhelms nerves, causing a localized numbing sensation. Capsaicin is also used in pepper spray.

Uses

K channel blocker; multiple sclerosis therapy

Chemical Properties

Crystalline solid, rectangular plates, or scales. Pungent odor and burning taste.

Chemical Properties

Off-White Crystalline Solid

Uses

A representative lot is a 5:1 E:Z mixture. It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.

Uses

analgesic (topical), depletes Substance P, neurotoxic

Waste Disposal

Do not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Noncombustible containers should be crushed and buried under more than 40 cm of soil. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office

Purification Methods

Recrystallise capcaicin from pet ether (b 40-60o), or pet ether/Et2O (9:1). Also purify it by chromatography on neutral Al2O3 (grade V) and elute successively with *C6H6, *C6H6/EtOAc (17:3) then *C6H6/EtOAc (7:3), and distil it at 120o/10-5mm, then repeatedly recrystallise the needles from isopropanol (charcoal). [Crombie et al. J Chem Soc 11025 1955, Bennett & Kirby J Chem Soc(C) 442 1968.] It causes pain and is neurotoxic [Bevan & Szolcsanyi Trends in Pharmacol Sci 11 330 1990, Beilstein 13 IV 2588].

Potential Exposure

Botanical animal and insect repellent used to repel birds, voles, deer, rabbits, squirrels, insects, and attacking dogs. Capsaicin, which is made from the Capsicum red chili pepper can be used indoors to protect carpets and upholstered furniture, and outdoors to protect fruit and vegetable crops, flowers, ornamental plants, shrubbery, trees, and lawns. It is also used in pepper sprays such as MACE, and as an analgesic in creams, lotions and solid sticks to reduce arthritic, postoperative and neuopathic pain, such as shingles. Capsaicin is obtained by grinding dried, ripe Capsicum frutescens L. chili peppers into a fine powder. The oleoresin is derived by distilling the powder in a solvent and evaporating the solvent. The resulting highly concentrated liquid has little odor but has an extremely pungent taste

Description

Capsaicin has a mild, warm-herbaceous odor and a burning pungent taste (at 10 ppm). It is used in compounded flavors for sauces where the pungent note is desired. This substance is present in several species of Capsicum (Family, Solanaceae). The sensation of pain, accompanied by irritation and inflammation, is due to substance P depletion from sensory (afferent) nerve fibers. These properties are used to study the physiology of pain and the effects as a counterirritant and gastrointestinal stimulant. This substance may be prepared from 3-chloro-2-isopropyltetrahydropyran; biosynthesis from Capsicum frutescens; separation form cis-capsaicin, pelargonic acid vanilamide, and dihydrocapsaicin, reaction of capsaicin.

Occurrence

The pungent principle in the fruits of various Capsicum species (Solanaceae)

Anticancer Research

Capsaicin is the major pungent ingredient in red and green chili pepper. It is reportedto induce apoptosis selectively in cancer cells and can suppress the activation ofNF-κB through suppression of NF-κB inhibitor IκBα (Aggarwal and Shishodia 2004). It shows anticancer effects in animal models and suppresses carcinogenesisin colon, skin, lung, tongue, and prostate cancers by altering the metabolism ofcarcinogens. It selectively suppresses the human cancer cell growth of prostate,leukemic, glioma, gastric, and hepatic cancers. It inhibited the tumorigenesis linkedand IL-6-induced activation of STAT-3 and STAT3-regulated gene products likecyclin D1, Bcl-2, Bcl-xL, survivin, and VGEF. It arrests cells in G1 phase andinduces apoptosis (Aggarwal et al. 2008; Clark and Lee 2016).

Uses

Capsaicin analogue (C175680). It is used as a tool in neurobiological research. Prototype vanilloid receptor agonist. Topical analgesic.

Incompatibilities

Slowly hydrolyzes in water, releasing ammonia and forming acetate salts.

Application in Particular Diseases

In Osteoarthritis: Capsaicin, an extract of red peppers that causes release and ultimately depletion of substance P from nerve fibers, has been beneficial in providing pain relief in OA when applied topically over affected joints. It may be used alone or in combination with oral analgesics or NSAIDs. To be effective, capsaicin must be used regularly, and it may take up to 2 weeks to work. It is well tolerated, but some patients experience temporary burning or stinging at the site of application. Patients should be warned not to get the cream in their eyes or mouth and to wash their hands after application. Application of the cream, gel, or lotion is recommended four times daily, but tapering to twice-daily application may enhance long-term adherence with adequate pain relief.

Description

Capsaicin is the main chemical that makes chili peppers hot. Capsaicin is an animal repellent that is also used against insects and mites. Capsaicin was first registered for use in the United States in 1962. The U.S. Environmental Protection Agency considers it to be a biochemical pesticide because it is a naturally occurring substance. The chemical compound capsaicin (8-methyl-N-vanillyl-6-nonenamide) is the active component of chili peppers, which are plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue it comes in contact with. Capsaicin and several related compounds are called capsaicinoids and are produced as a secondary metabolite by chili peppers, probably as deterrents against herbivores. Pure capsaicin is a hydrophobic, colorless, odorless, crystalline to waxy compound.

Chemical Properties

N-(4-Hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide has a mild, warm-herbaceous odor and burning, pungent taste (10 ppm). It is used in compounded flavors for sauces where the pungent note is desired.
InChI:InChI=1/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+

404-86-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (M1149)  Capsaicin (Natural)  >60.0%(HPLC) 404-86-4 1g 965.00CNY Detail
Sigma-Aldrich (12084)  Capsaicin  analytical standard 404-86-4 12084-50MG-F 2,039.31CNY Detail

404-86-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name capsaicin

1.2 Other means of identification

Product number -
Other names (E)-Capsaicin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:404-86-4 SDS

404-86-4Synthetic route

Vanillylamin
1196-92-5

Vanillylamin

(E)-8-Methylnon-6-enoic acid chloride
95636-02-5

(E)-8-Methylnon-6-enoic acid chloride

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Stage #1: Vanillylamin With sodium hydrogencarbonate In chloroform; water at 20℃; for 0.75h;
Stage #2: (E)-8-Methylnon-6-enoic acid chloride In chloroform; water at 20 - 40℃; for 1h;
91%
In diethyl ether for 72h; Ambient temperature;
In diethyl ether 1.) RT, 2 h, 2.) reflux, 2 h; Yield given;
trans-8-methyl-6-nonenoic acid
59320-77-3

trans-8-methyl-6-nonenoic acid

vanillylamine hydrochloride
7149-10-2

vanillylamine hydrochloride

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Schlenk technique;75%
trans-8-methyl-6-nonenoic acid
59320-77-3

trans-8-methyl-6-nonenoic acid

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With thionyl chloride Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether;
Multi-step reaction with 2 steps
1: SOCl2 / 2 h / Heating
2: diethyl ether / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: SOCl2 / 2 h / Heating
2: diethyl ether
View Scheme
(E)-N-[(4β-D-glucopyranosyloxy)-3-methoxyphenylmethyl]-8-methylnon-6-enamide

(E)-N-[(4β-D-glucopyranosyloxy)-3-methoxyphenylmethyl]-8-methylnon-6-enamide

A

D-Glucose
2280-44-6

D-Glucose

B

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
at 37℃; for 16h; β-glucosidase; enzymatic hydrolysis of capsaicin glucoside with α- or β-glucosidase;
(E)-1-hydroxy-6-methylhept-4-ene
59721-82-3

(E)-1-hydroxy-6-methylhept-4-ene

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h
2: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h
3: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
4: 92 percent / aq. NaOH / methanol / 15 h / Heating
5: SOCl2 / 2 h / Heating
6: diethyl ether / 2 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: pyridine; phosphorus (III)-bromide
2: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad
3: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether
View Scheme
Methanesulfonic acid (E)-6-methyl-hept-4-enyl ester
179617-41-5

Methanesulfonic acid (E)-6-methyl-hept-4-enyl ester

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h
2: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
3: 92 percent / aq. NaOH / methanol / 15 h / Heating
4: SOCl2 / 2 h / Heating
5: diethyl ether / 2 h / Heating
View Scheme
(E)-methyl 8-methyl-6-nonenoate
112375-54-9

(E)-methyl 8-methyl-6-nonenoate

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / aq. NaOH / methanol / 15 h / Heating
2: SOCl2 / 2 h / Heating
3: diethyl ether / 2 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: aq. KOH / ethanol / 1 h / Heating
2: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
3: diethyl ether / 72 h / Ambient temperature
View Scheme
trans-6-methyl-hept-4-enoic acid ethyl ester
179617-47-1

trans-6-methyl-hept-4-enoic acid ethyl ester

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 86 percent / LiAlH4 / diethyl ether / 15 h / Ambient temperature
2: Et3N / CH2Cl2 / 1.) 0 deg C, 30 min, 2.) RT, 1 h
3: 1.) NaH, 2.) KI / 1.) DMF, THF, RT, 15 min, 2.) DMF, THF, 80 deg C, 3.5 h
4: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
5: 92 percent / aq. NaOH / methanol / 15 h / Heating
6: SOCl2 / 2 h / Heating
7: diethyl ether / 2 h / Heating
View Scheme
2-((E)-6-Methyl-hept-4-enyl)-malonic acid dimethyl ester
179617-42-6

2-((E)-6-Methyl-hept-4-enyl)-malonic acid dimethyl ester

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 86 percent / DMSO, NaCl / H2O / 3 h / 170 °C
2: 92 percent / aq. NaOH / methanol / 15 h / Heating
3: SOCl2 / 2 h / Heating
4: diethyl ether / 2 h / Heating
View Scheme
6-hydroxyhexanal lactol
93545-84-7

6-hydroxyhexanal lactol

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: KOtBu / dimethylformamide / Ambient temperature
2: HNO3, NaNO2 / 1 h / 75 °C
3: 78 percent / CrO3 / acetone
4: SOCl2 / 2 h / Heating
5: diethyl ether
View Scheme
(Z)-1-hydroxy-8-methylnon-6-ene
90369-18-9

(Z)-1-hydroxy-8-methylnon-6-ene

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: HNO3, NaNO2 / 1 h / 75 °C
2: 78 percent / CrO3 / acetone
3: SOCl2 / 2 h / Heating
4: diethyl ether
View Scheme
(E)-1-hydroxy-8-methylnon-6-ene
90369-20-3

(E)-1-hydroxy-8-methylnon-6-ene

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / CrO3 / acetone
2: SOCl2 / 2 h / Heating
3: diethyl ether
View Scheme
(5-carboxypentyl)triphenylphosphonium bromide
50889-29-7

(5-carboxypentyl)triphenylphosphonium bromide

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: t-BuOK / dimethylformamide / 15 h / Ambient temperature
2: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h
3: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h
View Scheme
Multi-step reaction with 4 steps
1: t-BuOK / dimethylformamide / 15 h / Ambient temperature
2: 2M NaNO2, 5M aq. HNO3 / 0.5 h / 70 - 75 °C
3: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h
4: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h
View Scheme
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0 °C
1.2: 12 h / 0 - 20 °C
2.1: sodium nitrite; nitric acid / water / 0.58 h / 75 °C
3.1: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 2 h / 20 °C / Schlenk technique
View Scheme
vanillin
121-33-5

vanillin

KOH-solution

KOH-solution

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate / 3 h / 180 °C
2: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h
View Scheme
(6Z)-8-methyl-6-nonaneneoic acid
31467-60-4

(6Z)-8-methyl-6-nonaneneoic acid

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2M NaNO2, 5M aq. HNO3 / 0.5 h / 70 - 75 °C
2: thionyl chloride / 1.) room temp., 8 h, 2.) 100 deg C, 0.5 h
3: diethyl ether / 1.) RT, 2 h, 2.) reflux, 2 h
View Scheme
Multi-step reaction with 2 steps
1: sodium nitrite; nitric acid / water / 0.58 h / 75 °C
2: triethylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 2 h / 20 °C / Schlenk technique
View Scheme
hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: conc. H2SO4 / Heating
2: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature
4: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C
5: aq. KOH / ethanol / 1 h / Heating
6: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
7: diethyl ether / 72 h / Ambient temperature
View Scheme
methyl 6-oxohexanoate
6654-36-0

methyl 6-oxohexanoate

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
2: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C
3: aq. KOH / ethanol / 1 h / Heating
4: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
5: diethyl ether / 72 h / Ambient temperature
View Scheme
methyl 6-hydroxycaproate
4547-43-7

methyl 6-hydroxycaproate

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature
3: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C
4: aq. KOH / ethanol / 1 h / Heating
5: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
6: diethyl ether / 72 h / Ambient temperature
View Scheme
Benzoic acid 1-(1-benzenesulfonyl-2-methyl-propyl)-5-methoxycarbonyl-pentyl ester

Benzoic acid 1-(1-benzenesulfonyl-2-methyl-propyl)-5-methoxycarbonyl-pentyl ester

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Na(Hg), MeOH / tetrahydrofuran / 8 h / -20 °C
2: aq. KOH / ethanol / 1 h / Heating
3: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min
4: diethyl ether / 72 h / Ambient temperature
View Scheme
2,3-dichlorotetrahydro-2H-pyran
5631-95-8

2,3-dichlorotetrahydro-2H-pyran

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: diethyl ether
2: sodium; diisopropyl ether
3: pyridine; phosphorus (III)-bromide
4: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad
5: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether
View Scheme
3-chloro-2-isopropyltetrahydropyran
59721-81-2

3-chloro-2-isopropyltetrahydropyran

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium; diisopropyl ether
2: pyridine; phosphorus (III)-bromide
3: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad
4: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether
View Scheme
(E)-7-bromo-2-methyl-3-heptene
59721-83-4

(E)-7-bromo-2-methyl-3-heptene

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / und Erwaermen des Reaktionsprodukts mit wss.Kalilauge und Erhitzen des nach dem Ansaeuern isolierten Reaktionsprodukts bis auf 180grad
2: SOCl2 / Behandeln des Reaktionsprodukts mit 4-Aminomethyl-2-methoxy-phenol in Aether
View Scheme
C44H75NO12P(1-)*Na(1+)

C44H75NO12P(1-)*Na(1+)

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid; secretory phospholipase A2 from venom of Agkistrodon piscivorus piscivorus; potassium chloride; calcium chloride at 50℃; pH=7.5; aq. buffer;
N-[(6-bromo-7-hydroxycoumarin-4-yl)methoxycarbonyl]dopamine
1221557-61-4

N-[(6-bromo-7-hydroxycoumarin-4-yl)methoxycarbonyl]dopamine

A

capsaicin
404-86-4

capsaicin

B

6-bnromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one
223420-41-5

6-bnromo-7-hydroxy-4-(hydroxymethyl)-2H-chromen-2-one

Conditions
ConditionsYield
With water Photolysis;
(E)-[8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl 2-methoxy-4-[(8-methylnon-6-enamido)methyl]phenyl carbonate
1221557-70-5

(E)-[8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxycoumarin-4-yl]methyl 2-methoxy-4-[(8-methylnon-6-enamido)methyl]phenyl carbonate

A

8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxy-4-(hydroxymethyl)coumarin
1221557-66-9

8-[bis(carboxymethyl)aminomethyl]-6-bromo-7-hydroxy-4-(hydroxymethyl)coumarin

B

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With water Photolysis;
4-hydroxymethyl-2-methoxyphenol
498-00-0

4-hydroxymethyl-2-methoxyphenol

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: oxygen / toluene / 3 h / 70 °C / Sealed tube
2.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
3.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
3.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 3 steps
1: oxygen / toluene / 3 h / 70 °C / Sealed tube
2: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
3: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
Multi-step reaction with 4 steps
1.1: oxygen / toluene / 3 h / 70 °C / Sealed tube
2.1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
3.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
4.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
4.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 4 steps
1: oxygen / toluene / 3 h / 70 °C / Sealed tube
2: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
3: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
4: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
Vanillylamin
1196-92-5

Vanillylamin

trans-8-methyl-6-nonenoic acid
59320-77-3

trans-8-methyl-6-nonenoic acid

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
With lipase In tert-Amyl alcohol at 45℃; for 48h; Molecular sieve; Enzymatic reaction;
4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone
61152-59-8

4-(4-hydroxyphenyl-3-methoxy)-4-hydroxy-2-butanone

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
2.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
2.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
2: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
vanillin
121-33-5

vanillin

capsaicin
404-86-4

capsaicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
2.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
2.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 2 steps
1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 22 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
2: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
Multi-step reaction with 3 steps
1.1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
2.1: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
3.1: sodium hydrogencarbonate / water; chloroform / 0.75 h / 20 °C
3.2: 1 h / 20 - 40 °C
View Scheme
Multi-step reaction with 3 steps
1: rac-Pro-OH / 24 h / 20 °C / Inert atmosphere
2: D-glucose; L-alanin; ammonium chloride; glucose dehydrogenase; amine transaminase; L-alanine dehydrogenase; NADH; sodium hydroxide / dimethyl sulfoxide / 90 h / 37 °C / pH 8.2 / Darkness; Enzymatic reaction
3: lipase / tert-Amyl alcohol / 48 h / 45 °C / Molecular sieve; Enzymatic reaction
View Scheme
capsaicin
404-86-4

capsaicin

butyryl chloride
141-75-3

butyryl chloride

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl butanoate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl butanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;96%
With triethylamine In dichloromethane at 20℃; for 13 - 21h; dark; Heating / reflux;95%
With triethylamine In dichloromethane at 20 - 45℃; for 24 - 32h; Heating / reflux;95%
With triethylamine In dichloromethane at 20℃; Reflux;95%
capsaicin
404-86-4

capsaicin

Stearoyl chloride
112-76-5

Stearoyl chloride

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl octadecanoate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl octadecanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;96%
capsaicin
404-86-4

capsaicin

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

capsaicin palmitate

capsaicin palmitate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 40℃; Darkness; Reflux; Large scale;95%
With triethylamine; dmap In dichloromethane at 20℃; for 13 - 21h; Heating / reflux;95%
capsaicin
404-86-4

capsaicin

propionyl chloride
79-03-8

propionyl chloride

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl propanoate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl propanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;94%
capsaicin
404-86-4

capsaicin

N-(4-methoxybenzyl)benzenesulfonimidoyl fluoride

N-(4-methoxybenzyl)benzenesulfonimidoyl fluoride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-(4-methoxybenzyl)benzene sulfonimidate

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-(4-methoxybenzyl)benzene sulfonimidate

Conditions
ConditionsYield
Stage #1: capsaicin With 1H-imidazole In dichloromethane at 20℃; for 0.0833333h;
Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; for 5h;
Stage #3: N-(4-methoxybenzyl)benzenesulfonimidoyl fluoride With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; acetonitrile at 60℃; for 10h; Sealed tube; Inert atmosphere;
94%
capsaicin
404-86-4

capsaicin

dihydrocapsaicin
19408-84-5

dihydrocapsaicin

Conditions
ConditionsYield
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 12h; Reagent/catalyst; Green chemistry; chemoselective reaction;93%
With platinum (IV) oxide hydrate; hydrogen In methanol at 20℃; under 760.051 Torr; for 7h; Solvent;85%
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 4h;
capsaicin
404-86-4

capsaicin

pivaloyl chloride
3282-30-2

pivaloyl chloride

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl 2,2-dimethylpropanoate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl 2,2-dimethylpropanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;92.5%
capsaicin
404-86-4

capsaicin

4-bromomethylphenylboronic acid pinacol ester
138500-85-3

4-bromomethylphenylboronic acid pinacol ester

C31H44BNO5

C31H44BNO5

Conditions
ConditionsYield
With potassium carbonate In acetone at 60℃; for 2h;90.5%
capsaicin
404-86-4

capsaicin

chloroacetyl chloride
79-04-9

chloroacetyl chloride

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-chloroacetate
1236876-87-1

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-chloroacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1h;90.3%
(1R,2S,5R)-menthyl chloroformate
14602-86-9

(1R,2S,5R)-menthyl chloroformate

capsaicin
404-86-4

capsaicin

(1S,2S,5R)-5-methyl-2-(methylethyl)cyclohexyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenoxy}formate
913290-19-4

(1S,2S,5R)-5-methyl-2-(methylethyl)cyclohexyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenoxy}formate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;87%
capsaicin
404-86-4

capsaicin

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methoxyphenoxy}formate
913290-18-3

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl {4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methoxyphenoxy}formate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;86.5%
capsaicin
404-86-4

capsaicin

acetyl chloride
75-36-5

acetyl chloride

O-acetylcapsaicin

O-acetylcapsaicin

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;86%
capsaicin
404-86-4

capsaicin

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

C25H30N2O3

C25H30N2O3

Conditions
ConditionsYield
Stage #1: capsaicin With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique;
83%
dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate

dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate

capsaicin
404-86-4

capsaicin

(E)-N-(3-methoxy-4-(4-nitrophenoxy)benzyl)-8-methylnon-6-enamide

(E)-N-(3-methoxy-4-(4-nitrophenoxy)benzyl)-8-methylnon-6-enamide

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Schlenk technique;83%
formic acid
64-18-6

formic acid

capsaicin
404-86-4

capsaicin

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl formate
913290-13-8

4-[((6E)-8-methylnon-6-enoylamino)methyl]-2-methyoxyphenyl formate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4h;80.2%
2-methyl-1-buten-4-ol
763-32-6

2-methyl-1-buten-4-ol

capsaicin
404-86-4

capsaicin

C23H35NO3

C23H35NO3

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene for 1.5h; Inert atmosphere; Reflux;79%
1-(prop-1-yn-1-yl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one

1-(prop-1-yn-1-yl)-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one

capsaicin
404-86-4

capsaicin

C28H34INO5

C28H34INO5

Conditions
ConditionsYield
With caesium carbonate In ethanol at 20℃; chemoselective reaction;77%
capsaicin
404-86-4

capsaicin

methyl chloroacetate
96-34-4

methyl chloroacetate

{2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-acetic acid methyl ester

{2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-acetic acid methyl ester

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium carbonate; sodium iodide In acetone for 6h; Heating / reflux;71.4%
With disodium hydrogenphosphate; potassium carbonate; sodium iodide In acetone for 6h; Heating / reflux;71.4%
capsaicin
404-86-4

capsaicin

N-ethylmethylalanine

N-ethylmethylalanine

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylalanine hydrochloride

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylalanine hydrochloride

Conditions
ConditionsYield
Stage #1: capsaicin; N-ethylmethylalanine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
70.2%
capsaicin
404-86-4

capsaicin

1-carboxy-N,N-dimethyl-1-phenylmethanaminiumchloride
58685-78-2

1-carboxy-N,N-dimethyl-1-phenylmethanaminiumchloride

C28H38N2O4*ClH

C28H38N2O4*ClH

Conditions
ConditionsYield
Stage #1: capsaicin; 1-carboxy-N,N-dimethyl-1-phenylmethanaminiumchloride With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
68.2%
capsaicin
404-86-4

capsaicin

2-([1,4'-bipiperidin]-1'-yl)propionic acid hydrochloride

2-([1,4'-bipiperidin]-1'-yl)propionic acid hydrochloride

C31H49N3O4*ClH

C31H49N3O4*ClH

Conditions
ConditionsYield
Stage #1: capsaicin; 2-([1,4'-bipiperidin]-1'-yl)propionic acid hydrochloride With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
63.2%
capsaicin
404-86-4

capsaicin

N,N-diethyl-L-isoleucine

N,N-diethyl-L-isoleucine

C28H46N2O4*ClH

C28H46N2O4*ClH

Conditions
ConditionsYield
Stage #1: capsaicin; N,N-diethyl-L-isoleucine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
60.5%
BOC-glycine
4530-20-5

BOC-glycine

capsaicin
404-86-4

capsaicin

C25H38N2O6

C25H38N2O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;60.5%
N-ethyl-N-methyl-glycine

N-ethyl-N-methyl-glycine

capsaicin
404-86-4

capsaicin

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylglycine hydrochloride

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl N-ethyl-N-methylglycine hydrochloride

Conditions
ConditionsYield
Stage #1: N-ethyl-N-methyl-glycine; capsaicin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
60.1%
capsaicin
404-86-4

capsaicin

N,N'-(3,3'-Bi-4-hydroxy-5-methoxybenzyl)di-8-methylnon-(E)-6-enamide
134386-10-0

N,N'-(3,3'-Bi-4-hydroxy-5-methoxybenzyl)di-8-methylnon-(E)-6-enamide

Conditions
ConditionsYield
With riboflavin In ethanol at 30℃; for 0.333333h; Irradiation; pH 5.0 (citrate buffer);60%
With Capsicum annuum var. annuum cell protein extract; dihydrogen peroxide In water at 30℃; for 1.25h; pH=7.0;
With dihydrogen peroxide; horseradish peroxidase In aq. buffer at 20℃; for 0.166667h; pH=5.5;
capsaicin
404-86-4

capsaicin

N-ethyl-N-isopropylglycine

N-ethyl-N-isopropylglycine

(E)-2-methoxy-4-((8-methylnon-6-enoylamino)methyl)phenyl N-ethyl-N-isopropylglycine hydrochloride

(E)-2-methoxy-4-((8-methylnon-6-enoylamino)methyl)phenyl N-ethyl-N-isopropylglycine hydrochloride

Conditions
ConditionsYield
Stage #1: capsaicin; N-ethyl-N-isopropylglycine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -5 - 20℃; for 2h;
Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 1h; pH=3 - 4;
59.3%
capsaicin
404-86-4

capsaicin

4-carbamothioylbenzoic acid
4989-36-0

4-carbamothioylbenzoic acid

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 4-carbamothioyl benzoate

(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 4-carbamothioyl benzoate

Conditions
ConditionsYield
Stage #1: capsaicin With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.333333h;
Stage #2: 4-thiocarbamoylbenzoic acid In dichloromethane
57.3%
ketoprofen
22071-15-4

ketoprofen

capsaicin
404-86-4

capsaicin

2-(3-benzoyl-phenyl)-propionic acid 2-methoxy-4-[(8-methylnon-6-enoylamino)-methyl]-phenyl ester
1224428-97-0

2-(3-benzoyl-phenyl)-propionic acid 2-methoxy-4-[(8-methylnon-6-enoylamino)-methyl]-phenyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 30 - 35℃;56.6%

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