- Statement of Changes in Beneficial Ownership (4)

FORM 4 [ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES	OMB APPROVAL OMB Number: 3235-0287 Estimated average burden hours per response... 0.5
	Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(f) of the Investment Company Act of 1940

1. Name and Address of Reporting Person * SIMBERG BRUCE	2. Issuer Name and Ticker or Trading Symbol 21ST CENTURY HOLDING CO [ TCHC ]	5. Relationship of Reporting Person(s) to Issuer (Check all applicable) __ X __ Director                      _____ 10% Owner _____ Officer (give title below)      __ X __ Other (specify below) Chairman of the Board
(Last)          (First)          (Middle) 14050 N.W. 14 STREET, SUITE 180	3. Date of Earliest Transaction (MM/DD/YYYY) 8/21/2012
(Street) SUNRISE, FL 33323 (City)        (State)        (Zip)	4. If Amendment, Date Original Filed (MM/DD/YYYY)	6. Individual or Joint/Group Filing (Check Applicable Line) _ X _ Form filed by One Reporting Person ___ Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security (Instr. 3)	2. Trans. Date	2A. Deemed Execution Date, if any	3. Trans. Code (Instr. 8)		4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	8/21/2012		P		1000	A	$5.0428	280865	D
Common Stock	8/21/2012		P		1000	A	$5.0884	281865	D
Common Stock	8/21/2012		P		2000	A	$5.09	283865	D
Common Stock	8/21/2012		P		1000	A	$5.094	284865	D
Common Stock	8/21/2012		P		1000	A	$5.0979	285865	D
Common Stock	8/21/2012		P		1000	A	$5.0999	286865	D
Common Stock	8/21/2012		P		2500	A	$5.10	289365	D
Common Stock	8/21/2012		P		400	A	$5.1599	289765	D
Common Stock	8/21/2012		P		2000	A	$5.1995	291765	D

Table II - Derivative Securities Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Trans. Date	3A. Deemed Execution Date, if any	4. Trans. Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Options	$13.17							12/6/2008   (1)	12/6/2013	Common Stock	500		500	D
Options	$12.58							1/30/2009   (1)	1/30/2014	Common Stock	4500		4500	D
Options	$4.73							1/2/2010   (2)	1/2/2019	Common Stock	25000		25000	D
Options	$2.45							8/22/2012   (2)	8/22/2021	Common Stock	10000		10000	D
Options	$4.40							4/6/2013   (2)	4/6/2022	Common Stock	15000		15000	D

Explanation of Responses:
( 1)	The options vest 20% per year.
( 2)	The options vest 33 1/3% per year.

Reporting Owners
Reporting Owner Name / Address	Relationships
	Director	10% Owner	Officer	Other
SIMBERG BRUCE 14050 N.W. 14 STREET SUITE 180 SUNRISE, FL 33323	X			Chairman of the Board

Signatures
/s/ Bruce F. Simberg		8/23/2012
** Signature of Reporting Person		Date

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
*	If the form is filed by more than one reporting person, see Instruction 4(b)(v).
**	Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note:	File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.