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67416-61-9

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  • China Largest factory Manufacturer Supply High Quality Acetyl-11-keto-β-boswellic acid CAS 67416-61-9

    Cas No: 67416-61-9

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67416-61-9 Usage

Description

3-acetyl-11-keto-β-Boswellic acid is a naturally occurring pentacyclic triterpene isolated from the gum resin exudate from the stem of the tree B. serrata (frankincense). It selectively inhibits 5-lipoxygenase (IC50 = 1.5 μM) in an enzyme-directed, nonredox, and noncompetitive manner. 3-acetyl-11-keto-β-Boswellic acid and other members of the boswellic acid family have been studied for potential use in the control of inflammatory diseases, including arthritis and cancer.

Uses

3-Acetyl-11-keto-β-boswellic Acid (AKBA), be used in the place of the non-steroidal anti-inflammatory drug. AKBA, also inhibits human gastric carcinoma growth through modulation of the Wnt/β-catenin signaling pathway. It can be used as an anticancer agent.

in vitro

akba exerted a time- and concentration -dependent cytotoxicity on androgen-independent prostate cancer cells. akba blocked proliferation and elicited apoptosis in the chemoresistant and androgen-independent human pc-3 prostate cancer cells by the release of mitochondrial cytochrome c and dna fragmentation. also, akba concentration-dependently inhibited nf-κb signaling, yet it did not directly affect the nf-κb binding to dna. additionally, akba suppressed inhibitor κb kinase and nf-κb-dependent antiapoptotic gene products in pc-3 cells [1].

in vivo

pc-3 xenotransplanted male nmri/nu-nu mice were injected intraperitoneally at 100 μmol/kg daily for three weeks. akba dampened growth and proliferation of pc-3 xenografts in nude mice and elicited apoptosis. moreover, compared with the control group, akba reduced the tumor volume and the invasiveness of the tumor into the surrounding tissues [1].

references

[1]. syrovets, t., gschwend, j., buchele, b., laumonnier, y., zugmaier, w., genze, f., & simmet, t. inhibition of iκb kinase activity by acetyl-boswellic acids promotes apoptosis in androgen-independent pc-3 prostate cancer cells in vitro and in vivo. journal of biological chemistry. 2004; 280(7): 6170-6180.

Check Digit Verification of cas no

The CAS Registry Mumber 67416-61-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,7,4,1 and 6 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 67416-61:
(7*6)+(6*7)+(5*4)+(4*1)+(3*6)+(2*6)+(1*1)=139
139 % 10 = 9
So 67416-61-9 is a valid CAS Registry Number.
InChI:InChI=1/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23-,24-,25+,26-,28-,29+,30-,31-,32-/m1/s1

67416-61-9 Well-known Company Product Price

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  • (1076261)  3-Acetyl-11-keto-β-boswellic acid  United States Pharmacopeia (USP) Reference Standard

  • 67416-61-9

  • 1076261-20MG

  • 9,574.11CNY

  • Detail
  • Sigma-Aldrich

  • (74607)  3-O-Acetyl-11-keto-β-boswellic acid  analytical standard

  • 67416-61-9

  • 74607-5MG

  • 4,045.86CNY

  • Detail

67416-61-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Acetyl-11-keto-b-boswellic acid

1.2 Other means of identification

Product number -
Other names 3-O-Acetyl-11-keto-β-boswellic acid

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

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More Details:67416-61-9 SDS

67416-61-9Synthetic route

β-boswellic acid
631-69-6, 3877-93-8

β-boswellic acid

11-keto-β-boswellic acid
17019-92-0

11-keto-β-boswellic acid

3-O-acetyl-β-boswellic acid
5968-70-7

3-O-acetyl-β-boswellic acid

acetic anhydride
108-24-7

acetic anhydride

acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

Conditions
ConditionsYield
Stage #1: β-boswellic acid; 11-keto-β-boswellic acid; 3-O-acetyl-β-boswellic acid; acetic anhydride With pyridine at 20 - 65℃; for 3h;
Stage #2: With chromium(VI) oxide; acetic anhydride In acetic acid at 40℃; for 2h; Product distribution / selectivity;
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

2-(dimethylamino)ethyl chloride
107-99-3

2-(dimethylamino)ethyl chloride

(2'-N,N-dimethylaminoethyl) 3-O-acetyl-11-keto-β-boswellate

(2'-N,N-dimethylaminoethyl) 3-O-acetyl-11-keto-β-boswellate

Conditions
ConditionsYield
With sodium carbonate In acetone at 60℃; for 2h; Heating / reflux;45%
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

C32H47ClO4

C32H47ClO4

Conditions
ConditionsYield
With thionyl chloride for 1h; Heating / reflux;
α-boswellic acid

α-boswellic acid

3-O-acetyl-α-boswellic acid

3-O-acetyl-α-boswellic acid

2-amino-2-deoxyglucose
3416-24-8

2-amino-2-deoxyglucose

β-boswellic acid
631-69-6, 3877-93-8

β-boswellic acid

11-keto-β-boswellic acid
17019-92-0

11-keto-β-boswellic acid

3-O-acetyl-β-boswellic acid
5968-70-7

3-O-acetyl-β-boswellic acid

acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

A

β-boswellic acid glucosamine salt

β-boswellic acid glucosamine salt

B

11-keto-β-boswellic acid glucosamine salt

11-keto-β-boswellic acid glucosamine salt

C

3-O-acetyl-β-boswellic acid glucosamine salt

3-O-acetyl-β-boswellic acid glucosamine salt

D

3-O-acetyl-11-keto-β-boswellic acid glucosamine salt

3-O-acetyl-11-keto-β-boswellic acid glucosamine salt

E

α-boswellic acid glucosamine salt

α-boswellic acid glucosamine salt

F

3-O-acetyl-α-boswellic acid glucosamine salt

3-O-acetyl-α-boswellic acid glucosamine salt

Conditions
ConditionsYield
In methanol; water at 20℃; for 1h; Product distribution / selectivity;
α-boswellic acid

α-boswellic acid

3-O-acetyl-α-boswellic acid

3-O-acetyl-α-boswellic acid

β-boswellic acid
631-69-6, 3877-93-8

β-boswellic acid

11-keto-β-boswellic acid
17019-92-0

11-keto-β-boswellic acid

3-O-acetyl-β-boswellic acid
5968-70-7

3-O-acetyl-β-boswellic acid

acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

D-(+)-glucosamine hydrochloride
66-84-2

D-(+)-glucosamine hydrochloride

A

β-boswellic acid glucosamine salt

β-boswellic acid glucosamine salt

B

11-keto-β-boswellic acid glucosamine salt

11-keto-β-boswellic acid glucosamine salt

C

3-O-acetyl-β-boswellic acid glucosamine salt

3-O-acetyl-β-boswellic acid glucosamine salt

D

3-O-acetyl-11-keto-β-boswellic acid glucosamine salt

3-O-acetyl-11-keto-β-boswellic acid glucosamine salt

E

α-boswellic acid glucosamine salt

α-boswellic acid glucosamine salt

F

3-O-acetyl-α-boswellic acid glucosamine salt

3-O-acetyl-α-boswellic acid glucosamine salt

Conditions
ConditionsYield
Stage #1: α-boswellic acid; 3-O-acetyl-α-boswellic acid; β-boswellic acid; 11-keto-β-boswellic acid; 3-O-acetyl-β-boswellic acid; acetyl-11-keto-beta-boswellic acid; D-(+)-glucosamine hydrochloride In methanol; water at 20℃; for 0.25h;
Stage #2: With potassium hydroxide In methanol; water at 20℃; for 1.17h; Product distribution / selectivity;
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

D-(+)-glucosamine hydrochloride
66-84-2

D-(+)-glucosamine hydrochloride

3-O-acetyl-11-keto-β-boswellic acid glucosamine salt

3-O-acetyl-11-keto-β-boswellic acid glucosamine salt

Conditions
ConditionsYield
Stage #1: acetyl-11-keto-beta-boswellic acid; D-(+)-glucosamine hydrochloride In methanol; water at 20℃; for 0.25h;
Stage #2: With potassium hydroxide In methanol; water at 20℃; for 1.17h; Product distribution / selectivity;
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

11-keto-β-boswellic acid
17019-92-0

11-keto-β-boswellic acid

Conditions
ConditionsYield
With methanol; potassium hydroxide; water
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

3α-acetoxy-4-cyano-11-keto-24-norurs-12-ene

3α-acetoxy-4-cyano-11-keto-24-norurs-12-ene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 1 h / Heating / reflux
2: ammonia / tetrahydrofuran / 1.08 h / 0 °C
3: thionyl chloride / 1,2-dichloro-ethane / 6 h / Heating / reflux
View Scheme
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

3α-acetoxy-4-amino-11-keto-24-norurs-12-ene

3α-acetoxy-4-amino-11-keto-24-norurs-12-ene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 1 h / Heating / reflux
2: ammonia / tetrahydrofuran / 1.08 h / 0 °C
3: sodium hypobromide / 1,4-dioxane; water / 2 h / 65 - 75 °C
View Scheme
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

3-acetoxy-11-keto-24-norurs-12-en-4-isocyanate

3-acetoxy-11-keto-24-norurs-12-en-4-isocyanate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 1 h / Heating / reflux
2: ammonia / tetrahydrofuran / 1.08 h / 0 °C
3: sodium hypobromide / water; acetone / 0.75 h / 70 - 75 °C
View Scheme
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

3-O-acetyl-11-keto-β-boswellic acid amide

3-O-acetyl-11-keto-β-boswellic acid amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / Heating / reflux
2: ammonia / tetrahydrofuran / 1.08 h / 0 °C
View Scheme
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

N-(3-O-acetyl-11-keto-β-boswelloyl)-hydrazide

N-(3-O-acetyl-11-keto-β-boswelloyl)-hydrazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / Heating / reflux
2: hydrazine / dichloromethane / 2.08 h / 0 °C
View Scheme
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

N-(3-O-acetyl-11-keto-β-boswelloyl)-2-aminoethanol

N-(3-O-acetyl-11-keto-β-boswelloyl)-2-aminoethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / Heating / reflux
2: dichloromethane / 2.08 h / 0 °C
View Scheme
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

N-(3-O-acetyl-11-ketoboswelloyl)-ethylenediamine

N-(3-O-acetyl-11-ketoboswelloyl)-ethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / Heating / reflux
2: dichloromethane / 1.08 h / 0 °C
View Scheme
acetyl-11-keto-beta-boswellic acid
67416-61-9

acetyl-11-keto-beta-boswellic acid

N-(3-O-acetyl-11-keto-β-boswelloyl)-piperazine

N-(3-O-acetyl-11-keto-β-boswelloyl)-piperazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 1 h / Heating / reflux
2: dichloromethane / 2.08 h / 0 °C
View Scheme

67416-61-9Downstream Products

67416-61-9Relevant articles and documents

NOVEL SALTS OF BOSWELLIC ACIDS AND SELECTIVELY ENRICHED BOSWELLIC ACIDS AND PROCESSES FOR THE SAME

-

Page/Page column 11-12, (2008/06/13)

The present invention relates to new salts or ion ion-pair complexes obtained by a reaction between boswellic acids or selectively enriched 3-O-acetyl-11-keto-?-boswellic acid (AKBA) or 11-keto-?-boswellic acid (KBA) compounds obtained through a new improved process, and an organic amine, more particularly with glucosamine. These salts or ion pair complexes are useful in nutraceuticals and in food supplements for anti-inflammatory and analgesic treatment of joints and cancer prevention or cancer therapeutic agents. These salts or ion pair complexes could also used in cosmetic or pharmaceutical composition for external body part or organ to treat inflammatory diseases or cancer.

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