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1096-38-4

1096-38-4

Identification

Synonyms:16,17-Didehydroprogesterone;16-Dehydroprogesterone;3,20-Dioxopregna-4,16-diene;NSC 11037;NSC 9785;D16-Progesterone;D4,16-Pregnadiene-3,20-dione;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin H332 Harmful if inhaled H351 Suspected of causing cancer

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
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  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:16-Dehydroprogesterone
  • Packaging:1g
  • Price:$ 275
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TRC
  • Product Description:16-Dehydroprogesterone
  • Packaging:250mg
  • Price:$ 90
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:PREGNA-4,16-DIENE-3,20-DIONE AldrichCPR
  • Packaging:1ea
  • Price:$ 115
  • Delivery:In stock
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  • Manufacture/Brand:ChemScene
  • Product Description:16-?Dehydroprogesterone 99.53%
  • Packaging:50mg
  • Price:$ 50
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:Pregna-4,16-diene-3,20-dione 95%
  • Packaging:5g
  • Price:$ 224
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:Pregna-4,16-diene-3,20-dione 95%
  • Packaging:25g
  • Price:$ 729
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:Pregna-4,16-diene-3,20-dione 95%
  • Packaging:10g
  • Price:$ 365
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:4,16-PREGNADIENE-3,20-DIONE 95.00%
  • Packaging:5G
  • Price:$ 1261.26
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:4,16-PREGNADIENE-3,20-DIONE 95.00%
  • Packaging:1G
  • Price:$ 975.45
  • Delivery:In stock
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  • Manufacture/Brand:AHH
  • Product Description:16-Dehydroprogesterone 98%
  • Packaging:5g
  • Price:$ 297
  • Delivery:In stock
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Relevant articles and documentsAll total 25 Articles be found

Synthesis of 16-dehydro-20-oxopregnanes from 17α,20-epoxy-23,24-dinorcholan-22-oic acids. Highly stereospecific oxirane → allyl alcohol isomerization of an epoxycarboxylic acid

Toro, Andras,Pallagi, Istvan,Ambrus, Gabor

, p. 7651 - 7654 (1994)

A microbial degradation product of natural sterols was converted into traditional precursor of steroid syntheses by a simple sequence. The title isomerization, the key step, was investigated to demonstrate a concerted mechanism, in which a cyclic transition state, involving the oxirane oxygen, the β- and γ-carbon, the γ-proton to be removed and the catalyst coordinated by the carboxylate group, is postulated.

Synthesis of fluorinated 3beta-hydroxypregn-5-en-20-one derivatives.

Pataki,Jensen

, p. 437 - 447 (1976)

Treatment of the unstable 3beta-hydroxy-20, 20-dimethoxypregn-5-ene 3-acetate with acetic anhydride at reflux temperature gave a mixture of 3beta-hydroxy-20-methoxypregna-5, 17(20)-diene and 3beta-hydroxy-20-methoxypregna-5, 20-diene 3-acetates. Fluorination of this mixture with perchloryl fluoride afforded after fractionated crystallization 3beta-hydroxy-17-fluoro-20-methoxypregna-5, 20-diene 3-acetate. Acid hydrolysis of the reaction mixture and subsequent chromatographic separation led to 3beta-hydroxy-17-fluoropregn-5-en-20-one 3-acetate and 3beta-hydroxy-21-fluoropregn-5-en-20-one 3-acetate. 3beta-Hydroxy-17-fluoro-20-methoxy-pregna-5, 20-diene 3-acetate did not react further with perchloryl fluoride even under forcing conditions. Fluorination of 3beta-hydroxy-20-(N-ethyl benzylamino)-pregna-5, 17(20)-diene gave 3beta-hydroxy-17, 21-difluoro-pregn-5-en-20-one, exclusively.

Synthesis and anti-cancer activity of chiral tetrahydropyrazolo[1,5-a]pyridine-fused steroids

Lopes, Susana M.M.,Sousa, Emanuel P.,Barreira, Luísa,Marques, Cátia,Rodrigues, Maria Jo?o,Pinho e Melo, Teresa M.V.D.

, p. 16 - 23 (2017)

Regio- and stereoselective synthesis of novel chiral 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine–fused steroids via [8π?+?2π] cycloaddition of diazafulvenium methides with steroidal scaffolds is reported. The biological evaluation of the new family of hexacyclic steroids as anti-cancer agents was also carried out. Hexacyclic steroids bearing a benzyl group at C-22, derived from 16-dehydropregnenolone and 16-dehydroprogesterone, show considerable cytotoxicity against EL4 (murine T-lymphoma) in contrast with the corresponding C-22-unsubstituted derivatives showing low cytotoxicity. Thus, results indicate that the presence of the benzyl group is important to ensure cytotoxicity.

-

Deghenghi,R.,Gaudry,R.

, p. 1553 - 1557 (1961)

-

Chemistry of N,P-acetals: Application to the synthesis of 20-ketosteroids

Stoelwinder,Van Zoest,Van Leusen

, p. 2249 - 2252 (1992)

-

Steroids 48. Synthesis of 16α-ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione from 17-substituted 3-methoxyestradiols

Lokoes, Magdalena,Bakos, Tamas,Vincze, Iren

, p. 185 - 189 (1993)

A new synthesis of 16α-ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione is described, starting from 17-cyano- and 17α-ethynyl-3-methoxyestra-1,3,5-(10)-trien-17-ols.Keywords: steroids; synthesis; 19-norpregnenes; A-aromatic pregnenes

Introduction of 20-Keto Side Chains in 17-Oxosteroids: Wittig-Horner-Emmons Reactions of (E)-17--3-methoxyandrosta-3,5-diene

Stoelwinder, Johannes,Leusen, Albert M. van

, p. 3687 - 3691 (1993)

The synthesis is described of a series of polyfunctional unsaturated Δ16,20-20-isocyanosteroids 5a-f by the Wittig-Horner-Emmons reaction of (E)-17 steroid 4 with several aldehydes and with acetone.Hydrolysis of the isocyanosteroids 5a-f with dilute sulfuric acid gave Δ16-20-ketosteroids 6a-f in high yield.Hydrolysis of 5a was also possible under neutral conditions, via the intermediate Δ16,20-20-isocyanatosteroid 7a, leading to A-ring protected 16-dehydroprogesterone 8a.The Wittig-Horner-Emmons reaction, together with the described hydrolyses, provides a new method for the introduction of steroid side chains.The method is particularly suited for side chains of different size, structure, and functionality.

Preparation method of 16-dehydroprogesterone

-

Paragraph 0034-0055, (2021/06/12)

The invention provides a preparation method of 16-dehydroprogesterone, and belongs to the technical field of organic synthesis. The preparation method of the 16-dehydroprogesterone provided by the invention comprises the following steps: mixing 17 alpha-hydroxyprogesterone, methylbenzene, water, acetic acid and semicarbazide hydrochloride, and carrying out elimination reaction to obtain the 16-dehydroprogesterone. The method provided by the invention is low in cost, high in product yield and purity and suitable for industrial large-scale production. Specifically, 17alpha-hydroxyprogesterone is taken as a raw material, and the raw material is low in price; toluene and water are used as solvents, semicarbazide hydrochloride is used as an elimination reagent, acetic acid is used as a catalyst, a reaction system is divided into a toluene layer and a water layer, the elimination reaction is specifically carried out in the water layer, and a product generated by the reaction is extracted to the toluene layer, so that the product yield and purity are prevented from being influenced by impurities generated by excessive reaction of the product.

Sensitized Aliphatic Fluorination Directed by Terpenoidal Enones: A "visible Light" Approach

Bume, Desta Doro,Harry, Stefan Andrew,Pitts, Cody Ross,Lectka, Thomas

, p. 1565 - 1575 (2018/02/09)

In our continued effort to address the challenges of selective sp3 C-H fluorination on complex molecules, we report a sensitized aliphatic fluorination directed by terpenoidal enones using catalytic benzil and visible light (white LEDs). This sensitized approach is mild, simple to set up, and an economical alternative to our previous protocol based on direct excitation using UV light in a specialized apparatus. Additionally, the amenability of this protocol to photochemical flow conditions and preliminary evidence for electron-transfer processes are highlighted.

On a pregnane - 16 - ene - 3, 20 - dione steroid derivatives preparation method

-

Paragraph 0071; 0072, (2018/01/04)

The invention relates to a preparation method for a pregna-16-ene-3, 20-dione steroid derivative (II). The method is characterized by: reacting 17alpha-ethynyl-17beta-hydroxysteroid derivative I with a reagent A or an organic solvent containing the reagent A to obtaining the derivative (II). The reaction temperature ranges from 25DEG C to a solvent reflux temperature, and the reagent A is a solution formed by dissolving 5%-15% of phosphorus pentoxide in methanesulfonic acid.

New process for synthesizing steroid 3-one-4-ene

-

Paragraph 0058; 0059, (2016/10/09)

The invention discloses a new process for synthesizing steroid 3-one-4-ene. The method comprises the steps: with steroid 3-hydroxy-5-ene as a starting material, in a nonprotic organic solvent, with air or oxygen as an oxidant and with a transition metal nitrate and a 2,2,6,6-tetramethylpiperidine-1-oxyl free radical or an analogue thereof as catalysts, oxidizing to obtain the steroid 3-one-4-ene. The method has the advantages of high yield, mild reaction conditions, easily controlled operation, low energy consumption, low cost, and safety; and the whole process is friendly to the environment, and is suitable for industrialization.

Process route upstream and downstream products

Process route

Progesterone
57-83-0

Progesterone

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

17-methyltestosterone
58-18-4

17-methyltestosterone

Pregnenolone
145-13-1

Pregnenolone

21-Hydroxyprogesterone
64-85-7

21-Hydroxyprogesterone

pregna-4,7-diene-3,20-dione
17398-60-6

pregna-4,7-diene-3,20-dione

pregnane-3,6,20-trione
30802-24-5

pregnane-3,6,20-trione

pregnane-3,20-dione
7350-00-7

pregnane-3,20-dione

Conditions
Conditions Yield
With Hortaea werneckii B-763 at all growth phases; In YNB growth medium; N,N-dimethyl-formamide; at 28 ℃; for 24h; Enzymatic reaction;
allopregnenolone
566-61-0

allopregnenolone

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

9-alpha-hydroxyandrost-4-ene-3,17-dione
560-62-3,23015-99-8

9-alpha-hydroxyandrost-4-ene-3,17-dione

5α-H-pregn-16-ene-3,20-dione
13164-11-9

5α-H-pregn-16-ene-3,20-dione

9α-Hydroxy-4,16-pregnadiene-3,20-dione
116256-54-3

9α-Hydroxy-4,16-pregnadiene-3,20-dione

Conditions
Conditions Yield
In water; dimethyl sulfoxide; at 28 ℃; for 21h; Rhodococcus sp. culture, maize extract, K2HPO4, NaH2PO4*12H2O, menadiol;
10%
33%
28%
5%
16-dehydropregnenolone
104010-41-5

16-dehydropregnenolone

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Conditions
Conditions Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; ferric nitrate; In dichloromethane; at 22 - 30 ℃; for 16h; Reagent/catalyst; Temperature; Large scale;
100%
With cyclohexanone; aluminum isopropoxide; In toluene; at 100 ℃; for 0.25h;
80.5%
17α-ethynyl-17β-hydroxy-4-androstene-3,11-dione
95282-94-3

17α-ethynyl-17β-hydroxy-4-androstene-3,11-dione

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Conditions
Conditions Yield
With Eaton′s Reagent; In cyclohexane; at 25 ℃; for 5h; Large scale;
85%
levonorgestrel
434-03-7

levonorgestrel

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Conditions
Conditions Yield
With trifluoroacetic acid; [Ru(η3-2-C3H4Me)(CO)(1,1'-(Ph2P)2-ferrocene)][SbF6]; In tetrahydrofuran; for 26h; Heating;
97%
With [Re(κ3-P,N,S-Ph2PCH2P{=NP(=S)(OPh)2}Ph2)(CO)3]SbF6; In tetrahydrofuran; at 80 ℃; for 4.58333h; regioselective reaction; Microwave irradiation; Inert atmosphere;
91%
17-hydroxyprogesterone
68-96-2

17-hydroxyprogesterone

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Conditions
Conditions Yield
With semicarbazide hydrochloride; acetic acid; In toluene; at 80 - 90 ℃; for 6h; Reagent/catalyst; Temperature; Solvent;
82.1 g
20-isocyanato-20-tosylpregna-4,16-dien-3-one

20-isocyanato-20-tosylpregna-4,16-dien-3-one

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Conditions
Conditions Yield
With aluminum oxide; In dichloromethane; at 20 ℃; for 3h;
86%
20ξ-(Diethylphosphono)-20ξ-isocyano-3-methoxypregna-3,5,16-triene
139564-10-6

20ξ-(Diethylphosphono)-20ξ-isocyano-3-methoxypregna-3,5,16-triene

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Conditions
Conditions Yield
With perchloric acid; In 1,4-dioxane; for 12h; Heating;
86%
17-hexanoyloxy-pregn-4-ene-3,20-dione
630-56-8

17-hexanoyloxy-pregn-4-ene-3,20-dione

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Conditions
Conditions Yield
83%
3-Ethoxy-17-trifluormethansulfonyloxy-androsta-3,5,16-trien

3-Ethoxy-17-trifluormethansulfonyloxy-androsta-3,5,16-trien

ethyl vinyl ether
109-92-2,25104-37-4

ethyl vinyl ether

16-dehydroprogesterone
1096-38-4

16-dehydroprogesterone

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); triethylamine; In dimethyl sulfoxide; at 60 ℃; for 4h;
75%

Global suppliers and manufacturers

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  • Amadis Chemical Co., Ltd.
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  • Chemwill Asia Co., Ltd.
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  • Shanghai Upbio Tech Co.,Ltd
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  • Afine Chemicals Limited
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  • Country:China (Mainland)
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