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Ingenol

Ingenol Structure
Ingenol structure
CAS No.
30220-46-3
Chemical Name:
Ingenol
Synonyms
Ingeno;INGENOL;Inglenook;Ingenol, BR;(-)-Ingenol;Ingenol base;Ingenol >99%;Ingenol USP/EP/BP;INGENOL,HIGHPURITY;Ingenol 30220-46-3
CBNumber:
CB4370581
Molecular Formula:
C20H28O5
Molecular Weight:
348.43
MDL Number:
MFCD27980538
MOL File:
30220-46-3.mol
Last updated:2024-11-19 15:53:33
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Ingenol Properties

Melting point 153 °C
Boiling point 523.8±50.0 °C(Predicted)
Density 1.33±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility DMSO: soluble
form film
pka 12.06±0.70(Predicted)
color colorless
FDA UNII IC77UZI9G8

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS05
Signal word  Danger
Hazard statements  H315-H318
Precautionary statements  P280-P305+P351+P338
Hazard Codes  Xi
Risk Statements  38-41
Safety Statements  26-36
WGK Germany  3
HS Code  2914409000

Ingenol price More Price(41)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical I1112 Ingenol 30220-46-3 10MG $158 2024-03-01 Buy
TCI Chemical I1112 Ingenol 30220-46-3 50MG $475 2024-03-01 Buy
Cayman Chemical 14031 Ingenol ≥98% 30220-46-3 500μg $34 2024-03-01 Buy
Cayman Chemical 14031 Ingenol ≥98% 30220-46-3 1mg $59 2024-03-01 Buy
Cayman Chemical 14031 Ingenol ≥98% 30220-46-3 5mg $249 2024-03-01 Buy
Product number Packaging Price Buy
I1112 10MG $158 Buy
I1112 50MG $475 Buy
14031 500μg $34 Buy
14031 1mg $59 Buy
14031 5mg $249 Buy

Ingenol Chemical Properties,Uses,Production

Description

Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus.1 It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.

Chemical Properties

Isolated in 1968, ingenol, a highly oxygenated tetracyclic diterpene classified as a member of the phorboid family, is the parent compound of several dozen naturally occurring ingenanes that possess the same carbon skeleton but varied peripheral functionalities. In addition to their intriguing “inside-outside” bridged BC ring system, the ingenanes display interesting biological profiles that range from tumorpromoting to anti-leukemic and anti-HIV activities. Since the early 1980s, this combination of important biological function and complex architecture has inspired the efforts of numerous synthetic chemists.4 Previously, we reported an approach toward 1 wherein known â-ketoester 2 was advanced to diene 3, which served as a ring-closing metathesis substrate in a first generation Grubbs reaction that delivers the ingenane tetracycle 4.
Grubbs reaction

Ingenol mebutate

Ingenol mebutate is a selective small-molecule activator of protein kinase C (PKC) isolated from the plant Euphorbia peplus with potential antineoplastic activity. Ingenol mebutate activates various protein kinase C (PKC) isoforms, thereby inducing apoptosis in some tumor cells, including myeloid leukemia cells, melanoma cells, and basal cell carcinoma cells. The PKC family consists of signaling isoenzymes that regulate many cell processes including proliferation, differentiation, and apoptosis.
Ingenol mebutate was approved by the FDA in January 2012, and it is marketed under the name Picato®. Picato gel is indicated for the topical treatment of actinic keratosis. Before approval, ingenol mebutate was called PEP005 as an investigational drug. PEP005 is a selective small molecule activator of protein kinase C (PKC) extracted from the plant Euphorbia peplus, whose sap has been used as a traditional medicine for the treatment of skin conditions including warts and cancer. PEP005 also has potent anti-leukemic effects, inducing apoptosis in myeloid leukemia cell lines and primary AML cells at nanomolar concentrations.
Ingenol mebutate gel (Picato) is a topical cream that the manufacturer is requesting to use as a secondline treatment in patients with actinic keratosis (AK) who have failed or are intolerant to 5-fluorouracil (5-FU). Ingenol mebutate gel is available in two strengths – a 0.015% dose for lesions on the face and scalp and a 0.05% dose for lesions on the trunk and extremities.

Pharmacokinetics & metabolism

The pharmacokinetics investigation of the systemic absorption of ingenol mebutate gel 0.05% was evaluated in a randomized vehicle-controlled double blind study, in which 1 g was applied to a contiguous 100 cm2 area of multiple AKs on the dorsal forearms of 16 patients in two consecutive daily applications. This clinical trial showed that there was no detectable systemic absorption of the parent drug or its two principal metabolites (both acyl isomers of ingenol mebutate), when the limit of detection was 0.1 ng/ml.
In vitro studies using [3H]-ingenol mebutate showed that metabolism of the drug by human hepatocytes is extensive. Other in vitro studies showed that ingenol mebutate neither induces human CYPP450 enzymes CYP1A2, 2C9 and 3A4a, nor inhibits CYP1A2, 2A6, 2B6, 2C8, 2C9, 2C19, 2D6, 2E1 and 3A4.

Description

Ingenol is a diterpenoid related to phorbol, derived from the milkweed plant E. peplus. It is a protein kinase C activator that displays a Ki value of 30 μM and an ED50 value of 27 μM in vitro. Most ingenol esters are tumor-promoting. However, ingenol mebutate possesses anti-tumor activity when used topically for actinic keratosis.

Uses

Ingenol, is the analogue of Ingenol 3-Angelate (I655800), which has anti-tumor activity when used topically for the treatment of actinic keratosis.

Definition

ChEBI: A tetracyclic diterpenoid that is 1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one substituted at positions 5, 5a and 6 by hydroxy groups, positions 1, 1, 7 and 9 by met yl groups, position 4 by a hydroxymethyl group and position 1 by an oxo group (the 1aR,2S,5R,5aR,6S,8aS,9R,10aR diastere mer).

Ingenol synthesis

54706-99-9
30220-46-3
Synthesis of Ingenol from 20-DEOXYINGENOL

Ingenol Preparation Products And Raw materials

Raw materials

1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one, 4-[(acetyloxy)methyl]-1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-1,1,7,9-tetramethyl-, (1aR,2S,5R,5aR,6S,8aS,9R,10aR)- 20-DEOXYINGENOL Ingenol mebutate

Preparation Products

(1aR)-5β,6β-Bis(benzoyloxy)-1aα,2,5,5a,6,9,10,10aα-octahydro-5aβ-hydroxy-4-(hydroxymethyl)-1,1,7,9α-tetramethyl-1H-2α,8aα-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one

Ingenol Suppliers

Global( 238)Suppliers
Supplier Tel Email Country ProdList Advantage
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897 sales@biopurify.com China 3772 58
Hangzhou FandaChem Co.,Ltd. 		+8615858145714 FandaChem@Gmail.com China 9214 55
Shanghai Zheyan Biotech Co., Ltd. 		18017610038 zheyansh@163.com CHINA 3619 58
career henan chemical co 		+86-0371-86658258 +8613203830695 sales@coreychem.com China 29884 58
Shaanxi Pioneer Biotech Co., Ltd . 		+8613259417953 sales@pioneerbiotech.com China 3000 58
NanJing Spring & Autumn Biological Engineering CO., LTD. 		+8613815430202 sale02@cqherb.com CHINA 376 58
Chongqing Chemdad Co., Ltd 		+86-023-6139-8061 +86-86-13650506873 sales@chemdad.com China 39894 58
Shanghai Standard Technology Co., Ltd. 		18502101150 ft-sales@nature-standard.com CHINA 1923 58
Neostar United (Changzhou) Industrial Co., Ltd. 		+86-0519-85551759 +8613506123987 marketing1@neostarunited.com China 8838 58
Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd. 		+86-0086-025-69916489 +86-18852044786 tongyuansales@vip.sina.com China 323 58
Supplier Advantage
Chengdu Biopurify Phytochemicals Ltd.
58
Hangzhou FandaChem Co.,Ltd. 		55
Shanghai Zheyan Biotech Co., Ltd. 		58
career henan chemical co 		58
Shaanxi Pioneer Biotech Co., Ltd . 		58
NanJing Spring & Autumn Biological Engineering CO., LTD. 		58
Chongqing Chemdad Co., Ltd 		58
Shanghai Standard Technology Co., Ltd. 		58
Neostar United (Changzhou) Industrial Co., Ltd. 		58
Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd. 		58

Related articles

  • Total Synthesis of Ingenol
  • Isolated in 1968, ingenol (1), a highly oxygenated tetracyclic diterpene classified as a member of the phorboid family, is the....
  • Oct 30，2019

View Lastest Price from Ingenol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ingenol pictures 2024-11-19 Ingenol
30220-46-3
 US $44.00-129.00 / mg 99.87% 10g TargetMol Chemicals Inc.
Ingenol pictures 2024-11-14 Ingenol
30220-46-3
 US $1788.00 / KG 1KG 99% 100kg Baoji Guokang Bio-Technology Co., Ltd.
Ingenol pictures 2023-04-04 Ingenol
30220-46-3
 US $400.00 / KG 1KG 99% 10kg Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd.
  • Ingenol pictures
  • Ingenol
    30220-46-3
  • US $44.00-129.00 / mg
  • 99.87%
  • TargetMol Chemicals Inc.
  • Ingenol pictures
  • Ingenol
    30220-46-3
  • US $1788.00 / KG
  • 99%
  • Baoji Guokang Bio-Technology Co., Ltd.
  • Ingenol pictures
  • Ingenol
    30220-46-3
  • US $400.00 / KG
  • 99%
  • Nanjing Sky Hope Tongyuan Biological Engineering Co., Ltd.

30220-46-3(Ingenol)Related Search:

CYCLOHEPTENE CYCLOOCTANONE Cyclooctane 2,2,4-TRIMETHYL-3-PENTANONE Cycloheptanone
1-NONEN-3-OL (R)-(-)-1-OCTEN-3-OL, 99 CYCLOOCTANEMETHANOL 3-BUTENE-1,2-DIOL ADOXAL
3,5-DIMETHYL-4-OCTANONE 2-TERT-BUTYLPROPANE-1,3-DIOL Ingenol 3,5-DIMETHYL-4-HEPTANONE CYCLOPROPYLACETALDEHYDE
1-HYDROXYMETHYL-3-CYCLOPENTENE 2,2-DIMETHYL-3-OCTANONE (HYDROXYMETHYL)CYCLOHEPTANE

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1A,2,5,5A,6,9,10,10A OCTAHYDRO-5,5A,6-TRIHYDROXY4(HYDROXYMETHYL)1,1,7,9-TETRAMETHYL1H-2,8 AMETHANOCYCLOPENTA[A]CYCLOPROPA[E]CYCLODECEN-11 ONE 1 ALPHA,2,5,5 ALPHA,6,9,10,10 ALPHA-OCTAHYDRO-5,5 ALPHA,6-TRIHYDROXY-4-HYDROXYMETHYL-1,1,7,9-RETRAMETHYL-1H-2,8 ALPHA-M INGENOL INGENOL \ ACTIVATES PROTEIN KINASE C (1ar,2s,5r,5ar,6s,8as,9r,10ar)-1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1h-2,8a-methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one INGENOL,HIGHPURITY 1alpha,2,5,5alpha,6,9,10,10alpha-Octahydro-5,5alpha,6-trihydroxy-4-hydroxymethyl-1,1,7,9,-retramethyl-1H-2,8alpha-m (1aR,2S,8aS)-1aα,2,5,5a,6,9,10,10aα-Octahydro-5β,5aβ,6β-trihydroxy-4-(hydroxymethyl)-1,1,7,9α-tetramethyl-2,8aα-methano-1H-cyclopenta[a]cyclopropa[e]cyclodecene-11-one (1aR,2S,8aS)-1aα,2,5,5a,6,9,10,10aα-Octahydro-5β,5aβ,6β-trihydroxy-4-hydroxymethyl-1,1,7,9α-tetramethyl-1H-2,8aα-methanocyclopenta[a]cyclopropa[e]cyclodecene-11-one Ingenol >99% Ingenol base (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-Trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one 1H-2,8a-Methanocyclopenta[a]cyclopropa[e]cyclodecen-11-one,1a,2,5,5a,6,9,10,10a-octahydro-5,5a,6-trihydroxy-4-(hydroxyMethyl)-1,1,7,9-tetraMethyl-,(1aR,2S,5R,5aR,6S,8aS,9R,10aR)- Ingenol 30220-46-3 HPLC 99% purity Ingenol from Euphorbia lathyris 30220-46-3 99% Purity Ingenol Natural Plant Extracts 30220-46-3 Euphorbia Source Ingenol, BR Ingenol USP/EP/BP Inglenook (-)-Ingenol Ingeno Giant Euphorbia Alcohol (1S,4S,5R,6R,9S,10R,12R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one 30220-46-3 BioChemical Cell Signaling and Neuroscience Cell Biology Protein Phosphorylation Protein Kinase Activators Activator