(Z)-CAPSAICIN
- CAS No.
- 25775-90-0
- Chemical Name:
- (Z)-CAPSAICIN
- Synonyms
- civamide;Zucapsaicin;(Z)-CAPSAICIN;cis-capsaicin;cis-Capsaicine;(z)-6-nonenamid;Zucapsaicin,civaMide;Civamide cis-Capsaicin;(Z)-Capsaicin、Civamide;Civamide (Zucapsaicin)
- CBNumber:
- CB1694480
- Molecular Formula:
- C18H27NO3
- Molecular Weight:
- 305.41
- MDL Number:
- MFCD00209942
- MOL File:
- 25775-90-0.mol
- MSDS File:
- SDS
| Melting point | 70 °C |
|---|---|
| Boiling point | 511.5±50.0 °C(Predicted) |
| Density | 1.041±0.06 g/cm3(Predicted) |
| storage temp. | 2-8°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | 9.76±0.20(Predicted) |
| color | White to Off-White |
| Stability | Light Sensitive |
| FDA UNII | 15OX67P384 |
| ATC code | M02AB02 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |    GHS08,GHS05,GHS06 |
|---|---|
| Signal word | Danger |
| Hazard statements | H301-H335-H334-H317-H318-H315 |
| Precautionary statements | P280-P305+P351+P338-P310-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P261-P285-P304+P341-P342+P311-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P270-P301+P310-P321-P330-P405-P501 |
| Toxicity | LD50 intraperitoneal in mouse: 25mg/kg |
(Z)-CAPSAICIN price More Price(26)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Usbiological | 267862 | cis-Capsaicin | 25775-90-0 | 1mg | $489 | 2021-12-16 | Buy |
| TRC | C175690 | cis-Capsaicin | 25775-90-0 | 1g | $870 | 2021-12-16 | Buy |
| Matrix Scientific | 098870 | (Z)-N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-6-enamide 95+% | 25775-90-0 | 5g | $656 | 2021-12-16 | Buy |
| American Custom Chemicals Corporation | API0007177 | ZUCAPSAICIN 95.00% | 25775-90-0 | 10MG | $750.75 | 2021-12-16 | Buy |
| Ark Pharm | AK113725 | Zucapsaicin 95% | 25775-90-0 | 250mg | $130 | 2021-12-16 | Buy |
(Z)-CAPSAICIN Chemical Properties,Uses,Production
Description
Zucapsaicin is a topical analgesic that was approved in Canada in July 2010 for use in conjunction with oral COX-2 inhibitors or NSAIDs to relieve severe pain in adults with osteoarthritis of the knee. Zucapsaicin is the cis-isomer of the natural product capsaicin. Capsaicin is available without a prescription in creams, lotions, and patches for the treatment of neuropathic and musculoskeletal pain. Zucapsaicin is available as a 0.075% by weight cream. The advantages of zucapsaicin compared with capsaicin are reported to be a lesser degree of local irritation (stinging, burning, erythema) in patients and a greater degree of efficacy in preclinical animal models of pain. The analgesic action of zucapsaicin and capsaicin is mediated through the transient receptor potential vanilloid type 1 (TRPV1) channel.
Originator
E Merck AG (Germany)
Uses
(Z)-CAPSAICIN is used as a tool in neurobiological research. Prototype vanilloid receptor agonist.
Definition
ChEBI: Zucapsaicin is a member of phenols and a member of methoxybenzenes.
brand name
Civanex
Clinical Use
Zucapsaicin, the cis-isomer of the natural product capsaicin, is a topical analgesic that was initially developed by Winston Pharmaceuticals and approved in Canada in July 2010 for the treatment of severe pain in adults with osteoarthritis of the knee. The advantages of zucapsaicin compared with naturally-occurring capsaicin are reported to be a lesser degree of local irritation (stinging, burning, erythema) in patients and a greater degree of efficacy in preclinical animal models of pain. The analgesic action of both zucapsaicin and capsaicin is mediated through the transient receptor potential vanilloid type 1 (TRPV1) channel, a ligand-gated ion channel expressed in the spinal cord, brain, and localized on neurons in sensory projections to the skin, muscles, joints, and gut.
Synthesis
The scale preparation of zucapsaicin likely parallels the original approach described by Gannett and co-workers involving the coupling of vanillylamine with (Z)-8-methylnon-6-enoyl chloride. 216 Orito and co-workers elaborated this original approach in an effort to prepare both capsaicin and zucapsaicin on gram-scale, and this route is described in the scheme.
Commercial 6-bromohexanoic acid (285) was activated as the Wittig salt prior to condensation with isobutylaldehyde in the presence of strong base to generate an 11:1 ratio of E/Z-olefinic acids favoring Z-isomer 286. Removal of the minor isomer was easily achieved by short-path distillation.217 Interestingly, the authors reported that facile olefin isomerization of 286 occurred upon exposure to nitric acid at elevated temperatures, converting 286 to the corresponding E-isomer. Recrystallization provided the product on multi-gram scale in 77% yield, representing a possible scale production method for capsaicin. For the preparation of zucapsaicin, acid 286 was converted the acid chloride via thionyl chloride followed by immediate condensation with commercially available vanillylamine (287). Two recrystallization steps were subsequently employed to produce gram-scale amounts of zucapsaicin (XXVI) in 66% yield overall for the two-step process.
(Z)-CAPSAICIN Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hebei Mojin Biotechnology Co., Ltd | +8613288715578 | sales@hbmojin.com | China | 12456 | 58 |
| Ouhuang Engineering Materials (Hubei) Co., Ltd | +8617702722807 | admin@hbouhuang.com | China | 1696 | 58 |
| career henan chemical co | +86-0371-86658258 | sales@coreychem.com | China | 29914 | 58 |
| Hubei Jusheng Technology Co.,Ltd. | 18871490254 | linda@hubeijusheng.com | CHINA | 28180 | 58 |
| Hebei Guanlang Biotechnology Co., Ltd. | +86-19930503282 | alice@crovellbio.com | China | 8823 | 58 |
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| Chongqing Chemdad Co., Ltd | +86-023-61398051 +8613650506873 | sales@chemdad.com | China | 39916 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| Shanxi Xuanran Import and Export Trade Co., Ltd. | +8617735180244 | mike_yan@xuanranglobal.com | CHINA | 4022 | 58 |
| changzhou huayang technology co., ltd | +8615250961469 | 2571773637@qq.com | China | 9821 | 58 |
View Lastest Price from (Z)-CAPSAICIN manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-04-24 | (Z)-Capsaicin
25775-90-0
|
US $15.00 / kg | 1kg | 99.912% | 10ton | Ouhuang Engineering Materials (Hubei) Co., Ltd | |
 |
2023-07-04 | (Z)-CAPSAICIN
25775-90-0
|
US $0.00 / KG | 1KG | 99% | 50000KG/month | Hebei Mojin Biotechnology Co., Ltd | |
 |
2021-06-11 | (Z)-CAPSAICIN / Zucapsaicin
25775-90-0
|
US $1.00 / PCS | 1KG | 99% | 10 mt | Hebei Guanlang Biotechnology Co., Ltd. |
-
- (Z)-Capsaicin
25775-90-0
- US $15.00 / kg
- 99.912%
- Ouhuang Engineering Materials (Hubei) Co., Ltd
-
- (Z)-CAPSAICIN
25775-90-0
- US $0.00 / KG
- 99%
- Hebei Mojin Biotechnology Co., Ltd
-
- (Z)-CAPSAICIN / Zucapsaicin
25775-90-0
- US $1.00 / PCS
- 99%
- Hebei Guanlang Biotechnology Co., Ltd.
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